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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (12) Show 21 proteins XML

enzymes (9)transporters (12) Show 21 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015151

Secondary Accession Numbers

HMDB15151

Metabolite Identification

Common Name

Glyburide

Description

Glyburide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Glyburide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Glyburide appears to be completely metabolized, likely in the liver. Although its metabolites exert a small hypoglycemic effect, their contribution to glyburide's hypoglycemic effect is thought to be clinically unimportant. Glyburide metabolites are excreted in urine and feces in approximately equal proportions. The half-life of glyburide appears to be unaffected in those with a creatinine clearance of greater than 29 ml/min/1.73m².

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1016
  Mrv0541 02231215102D          

 33 35  0  0  0  0            999 V2000
    5.2224   -5.5689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 18  1  0  0  0  0
  3 17  2  0  0  0  0
  6 26  2  0  0  0  0
  7 28  1  0  0  0  0
  7 33  1  0  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  9 17  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0015151
     RDKit          3D
Glyburide
 61 63  0  0  0  0  0  0  0  0999 V2000
    6.8700   -1.2611    3.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -0.7407    2.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6240   -0.4591    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514   -0.7098    1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9977   -0.4580    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7671    0.0561   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0964    0.3831   -1.6893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4648    0.2992   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.0502   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0384    0.3499   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9152    0.8254   -1.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495    0.1754    0.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779    0.5366   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    0.2858    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    0.6768   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -0.2297   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748    0.1448   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358    1.4259   -1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5939    1.8693   -2.4570 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.5445    3.2992   -2.9243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    0.9930   -3.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9742    1.6676   -1.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925    0.4108   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0775   -0.5853   -1.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286    0.2674   -0.3847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712   -1.0128   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2252   -1.3728    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2280   -0.7270    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965   -1.1804    1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8062   -0.6022    0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7842   -1.0382   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.3524   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.9670   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349   -2.2318    3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5574   -0.6009    3.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8978   -1.4187    3.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1231   -1.1203    2.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0340   -0.6578    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.7108   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.1931    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    1.5971   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -0.0483   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.9426    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.7781    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8376   -1.2340   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2152   -0.5736   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    2.5045   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911    1.1591    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043   -1.7710   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2035   -1.0548    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -2.4632    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0639   -1.1107    3.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394    0.3808    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3345   -0.6901    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6245   -2.2691    1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8388    0.4998    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8128   -0.9206    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0927   -2.0371   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8429   -0.3452   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.3749   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    2.6899    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 18 32  1  0
 32 33  2  0
  9  3  1  0
 33 15  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  8 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END

1016
  Mrv0541 02231215102D          

 33 35  0  0  0  0            999 V2000
    5.2224   -5.5689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 18  1  0  0  0  0
  3 17  2  0  0  0  0
  6 26  2  0  0  0  0
  7 28  1  0  0  0  0
  7 33  1  0  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  9 17  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015151

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

> <INCHI_KEY>
ZNNLBTZKUZBEKO-UHFFFAOYSA-N

> <FORMULA>
C23H28ClN3O5S

> <MOLECULAR_WEIGHT>
494.004

> <EXACT_MASS>
493.143819418

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.75337429229601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.7911100480000006

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.717745987330456

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.320179892066342

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1594498864691096

> <JCHEM_POLAR_SURFACE_AREA>
113.60000000000001

> <JCHEM_REFRACTIVITY>
126.9801

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyburide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015151
     RDKit          3D
Glyburide
 61 63  0  0  0  0  0  0  0  0999 V2000
    6.8700   -1.2611    3.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -0.7407    2.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6240   -0.4591    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514   -0.7098    1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9977   -0.4580    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7671    0.0561   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0964    0.3831   -1.6893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4648    0.2992   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.0502   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0384    0.3499   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9152    0.8254   -1.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495    0.1754    0.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779    0.5366   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    0.2858    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    0.6768   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -0.2297   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748    0.1448   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358    1.4259   -1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5939    1.8693   -2.4570 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.5445    3.2992   -2.9243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    0.9930   -3.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9742    1.6676   -1.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925    0.4108   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0775   -0.5853   -1.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286    0.2674   -0.3847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712   -1.0128   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2252   -1.3728    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2280   -0.7270    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965   -1.1804    1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8062   -0.6022    0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7842   -1.0382   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.3524   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.9670   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349   -2.2318    3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5574   -0.6009    3.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8978   -1.4187    3.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1231   -1.1203    2.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0340   -0.6578    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.7108   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.1931    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    1.5971   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -0.0483   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.9426    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.7781    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8376   -1.2340   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2152   -0.5736   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    2.5045   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911    1.1591    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043   -1.7710   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2035   -1.0548    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -2.4632    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0639   -1.1107    3.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394    0.3808    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3345   -0.6901    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6245   -2.2691    1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8388    0.4998    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8128   -0.9206    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0927   -2.0371   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8429   -0.3452   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.3749   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    2.6899    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 18 32  1  0
 32 33  2  0
  9  3  1  0
 33 15  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  8 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1016                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.748 -10.395   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       9.748   3.465   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.416   5.005   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.208   3.465   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.289   3.465   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.748  -5.005   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.414  -7.315   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.082   7.315   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   5.005   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       8.415  -5.005   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      12.416   8.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.750   7.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416   9.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083   8.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.750  10.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.083   9.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   5.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.082  -0.385   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.081  -5.775   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.081  -7.315   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.748  -8.085   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415  -8.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.748  -9.625   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415  -9.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.081 -10.395   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080  -8.085   0.000  0.00  0.00           C+0
CONECT    1   31                                                            
CONECT    2    4    5    9   18                                             
CONECT    3   17                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6   26                                                            
CONECT    7   28   33                                                       
CONECT    8   11   17                                                       
CONECT    9    2   17                                                       
CONECT   10   25   26                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
CONECT   17    3    8    9                                                  
CONECT   18    2   21   22                                                  
CONECT   19   20   23   24                                                  
CONECT   20   19   25                                                       
CONECT   21   18   23                                                       
CONECT   22   18   24                                                       
CONECT   23   19   21                                                       
CONECT   24   19   22                                                       
CONECT   25   10   20                                                       
CONECT   26    6   10   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28    7   27   30                                                  
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31    1   29   32                                                  
CONECT   32   30   31                                                       
CONECT   33    7                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0015151
HETATM    1  C1  UNL     1       6.870  -1.261   3.355  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.625  -0.741   2.087  1.00  0.00           O  
HETATM    3  C2  UNL     1       7.624  -0.459   1.166  1.00  0.00           C  
HETATM    4  C3  UNL     1       8.951  -0.710   1.526  1.00  0.00           C  
HETATM    5  C4  UNL     1       9.998  -0.458   0.670  1.00  0.00           C  
HETATM    6  C5  UNL     1       9.767   0.056  -0.587  1.00  0.00           C  
HETATM    7 CL1  UNL     1      11.096   0.383  -1.689  1.00  0.00          CL  
HETATM    8  C6  UNL     1       8.465   0.299  -0.934  1.00  0.00           C  
HETATM    9  C7  UNL     1       7.379   0.050  -0.076  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.038   0.350  -0.544  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.915   0.825  -1.732  1.00  0.00           O  
HETATM   12  N1  UNL     1       4.849   0.175   0.168  1.00  0.00           N  
HETATM   13  C9  UNL     1       3.578   0.537  -0.472  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.416   0.286   0.448  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.183   0.677  -0.266  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.463  -0.230  -1.035  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.675   0.145  -1.691  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.136   1.426  -1.608  1.00  0.00           C  
HETATM   19  S1  UNL     1      -2.594   1.869  -2.457  1.00  0.00           S  
HETATM   20  O3  UNL     1      -2.545   3.299  -2.924  1.00  0.00           O  
HETATM   21  O4  UNL     1      -2.686   0.993  -3.685  1.00  0.00           O  
HETATM   22  N2  UNL     1      -3.974   1.668  -1.445  1.00  0.00           N  
HETATM   23  C15 UNL     1      -4.593   0.411  -1.222  1.00  0.00           C  
HETATM   24  O5  UNL     1      -4.077  -0.585  -1.811  1.00  0.00           O  
HETATM   25  N3  UNL     1      -5.729   0.267  -0.385  1.00  0.00           N  
HETATM   26  C16 UNL     1      -6.371  -1.013  -0.148  1.00  0.00           C  
HETATM   27  C17 UNL     1      -6.225  -1.373   1.302  1.00  0.00           C  
HETATM   28  C18 UNL     1      -7.228  -0.727   2.193  1.00  0.00           C  
HETATM   29  C19 UNL     1      -8.596  -1.180   1.729  1.00  0.00           C  
HETATM   30  C20 UNL     1      -8.806  -0.602   0.354  1.00  0.00           C  
HETATM   31  C21 UNL     1      -7.784  -1.038  -0.644  1.00  0.00           C  
HETATM   32  C22 UNL     1      -0.455   2.352  -0.858  1.00  0.00           C  
HETATM   33  C23 UNL     1       0.688   1.967  -0.202  1.00  0.00           C  
HETATM   34  H1  UNL     1       7.435  -2.232   3.264  1.00  0.00           H  
HETATM   35  H2  UNL     1       7.557  -0.601   3.952  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.898  -1.419   3.867  1.00  0.00           H  
HETATM   37  H4  UNL     1       9.123  -1.120   2.533  1.00  0.00           H  
HETATM   38  H5  UNL     1      11.034  -0.658   0.963  1.00  0.00           H  
HETATM   39  H6  UNL     1       8.258   0.711  -1.935  1.00  0.00           H  
HETATM   40  H7  UNL     1       4.810  -0.193   1.123  1.00  0.00           H  
HETATM   41  H8  UNL     1       3.629   1.597  -0.770  1.00  0.00           H  
HETATM   42  H9  UNL     1       3.415  -0.048  -1.397  1.00  0.00           H  
HETATM   43  H10 UNL     1       2.500   0.943   1.348  1.00  0.00           H  
HETATM   44  H11 UNL     1       2.415  -0.778   0.760  1.00  0.00           H  
HETATM   45  H12 UNL     1       0.838  -1.234  -1.092  1.00  0.00           H  
HETATM   46  H13 UNL     1      -1.215  -0.574  -2.280  1.00  0.00           H  
HETATM   47  H14 UNL     1      -4.386   2.505  -0.967  1.00  0.00           H  
HETATM   48  H15 UNL     1      -6.091   1.159   0.067  1.00  0.00           H  
HETATM   49  H16 UNL     1      -5.804  -1.771  -0.725  1.00  0.00           H  
HETATM   50  H17 UNL     1      -5.203  -1.055   1.630  1.00  0.00           H  
HETATM   51  H18 UNL     1      -6.270  -2.463   1.435  1.00  0.00           H  
HETATM   52  H19 UNL     1      -7.064  -1.111   3.222  1.00  0.00           H  
HETATM   53  H20 UNL     1      -7.139   0.381   2.224  1.00  0.00           H  
HETATM   54  H21 UNL     1      -9.335  -0.690   2.397  1.00  0.00           H  
HETATM   55  H22 UNL     1      -8.624  -2.269   1.771  1.00  0.00           H  
HETATM   56  H23 UNL     1      -8.839   0.500   0.445  1.00  0.00           H  
HETATM   57  H24 UNL     1      -9.813  -0.921   0.013  1.00  0.00           H  
HETATM   58  H25 UNL     1      -8.093  -2.037  -1.028  1.00  0.00           H  
HETATM   59  H26 UNL     1      -7.843  -0.345  -1.511  1.00  0.00           H  
HETATM   60  H27 UNL     1      -0.856   3.375  -0.815  1.00  0.00           H  
HETATM   61  H28 UNL     1       1.233   2.690   0.391  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   37
CONECT    5    6    6   38
CONECT    6    7    8
CONECT    8    9    9   39
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   16   33
CONECT   16   17   45
CONECT   17   18   18   46
CONECT   18   19   32
CONECT   19   20   20   21   21
CONECT   19   22
CONECT   22   23   47
CONECT   23   24   24   25
CONECT   25   26   48
CONECT   26   27   31   49
CONECT   27   28   50   51
CONECT   28   29   52   53
CONECT   29   30   54   55
CONECT   30   31   56   57
CONECT   31   58   59
CONECT   32   33   33   60
CONECT   33   61
END

HMDB0015151
     RDKit          3D
Glyburide
 61 63  0  0  0  0  0  0  0  0999 V2000
    6.8700   -1.2611    3.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -0.7407    2.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6240   -0.4591    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514   -0.7098    1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9977   -0.4580    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7671    0.0561   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0964    0.3831   -1.6893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4648    0.2992   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.0502   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0384    0.3499   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9152    0.8254   -1.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495    0.1754    0.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779    0.5366   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    0.2858    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    0.6768   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632   -0.2297   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748    0.1448   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358    1.4259   -1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5939    1.8693   -2.4570 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.5445    3.2992   -2.9243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    0.9930   -3.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9742    1.6676   -1.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925    0.4108   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0775   -0.5853   -1.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286    0.2674   -0.3847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712   -1.0128   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2252   -1.3728    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2280   -0.7270    2.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965   -1.1804    1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8062   -0.6022    0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7842   -1.0382   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.3524   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.9670   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349   -2.2318    3.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5574   -0.6009    3.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8978   -1.4187    3.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1231   -1.1203    2.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0340   -0.6578    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.7108   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.1931    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    1.5971   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -0.0483   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.9426    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.7781    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8376   -1.2340   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2152   -0.5736   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    2.5045   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911    1.1591    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8043   -1.7710   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2035   -1.0548    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -2.4632    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0639   -1.1107    3.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1394    0.3808    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3345   -0.6901    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6245   -2.2691    1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8388    0.4998    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8128   -0.9206    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0927   -2.0371   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8429   -0.3452   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    3.3749   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    2.6899    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 18 32  1  0
 32 33  2  0
  9  3  1  0
 33 15  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  8 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea	ChEBI
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea	ChEBI
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide	ChEBI
Diabeta	ChEBI
Glibenclamida	ChEBI
Glibenclamide	ChEBI
Glibenclamidum	ChEBI
Glynase	ChEBI
Micronase	ChEBI
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulphonyl)-3-cyclohexylurea	Generator
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulphonyl)-3-cyclohexylurea	Generator
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulphonyl)phenyl)ethyl)-2-methoxybenzamide	Generator
Apo-glibenclamide	HMDB
Euglucon 5	HMDB
Euglucon N	HMDB
Glybenclamide	HMDB
Neogluconin	HMDB
Maninil	HMDB
Daonil	HMDB

Chemical Formula

C₂₃H₂₈ClN₃O₅S

Average Molecular Weight

494.004

Monoisotopic Molecular Weight

493.143819418

IUPAC Name

5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

Traditional Name

glyburide

CAS Registry Number

10238-21-8

SMILES

COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1

InChI Identifier

InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

InChI Key

ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Anisole
Phenol ether
Methoxybenzene
Phenoxy compound
Chlorobenzene
Halobenzene
Sulfonylurea
Alkyl aryl ether
Aryl chloride
Aryl halide
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Ether
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:5441 )
N-sulfonylurea (CHEBI:5441 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015151)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Glibenclamide Action Pathway (PathBank: SMP0000460)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	169 - 170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0021 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	204.7	30932474
[M+H]+	Not Available	205.862	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000784

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0021 g/L	ALOGPS
logP	3.78	ALOGPS
logP	3.79	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.98 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	217.533	30932474
DeepCCS	[M-H]-	215.175	30932474
DeepCCS	[M-2H]-	248.541	30932474
DeepCCS	[M+Na]+	223.695	30932474
AllCCS	[M+H]+	210.9	32859911
AllCCS	[M+H-H2O]+	209.2	32859911
AllCCS	[M+NH4]+	212.5	32859911
AllCCS	[M+Na]+	213.0	32859911
AllCCS	[M-H]-	202.8	32859911
AllCCS	[M+Na-2H]-	204.0	32859911
AllCCS	[M+HCOO]-	205.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.75 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7503 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.25 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2434.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	242.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	551.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	574.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	192.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1253.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	591.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1668.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	302.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	134.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glyburide	COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1	5823.8	Standard polar	33892256
Glyburide	COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1	3224.8	Standard non polar	33892256
Glyburide	COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1	4251.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glyburide,1TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C	4244.4	Semi standard non polar	33892256
Glyburide,1TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C	3512.0	Standard non polar	33892256
Glyburide,1TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C	5599.3	Standard polar	33892256
Glyburide,1TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1	4162.7	Semi standard non polar	33892256
Glyburide,1TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1	3515.5	Standard non polar	33892256
Glyburide,1TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1	5573.3	Standard polar	33892256
Glyburide,1TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1	4139.3	Semi standard non polar	33892256
Glyburide,1TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1	3579.4	Standard non polar	33892256
Glyburide,1TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1	5510.4	Standard polar	33892256
Glyburide,2TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	4009.0	Semi standard non polar	33892256
Glyburide,2TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	3641.3	Standard non polar	33892256
Glyburide,2TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	5373.9	Standard polar	33892256
Glyburide,2TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	3981.9	Semi standard non polar	33892256
Glyburide,2TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	3694.6	Standard non polar	33892256
Glyburide,2TMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C1)[Si](C)(C)C	5238.1	Standard polar	33892256
Glyburide,2TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3969.3	Semi standard non polar	33892256
Glyburide,2TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3763.9	Standard non polar	33892256
Glyburide,2TMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1	5196.6	Standard polar	33892256
Glyburide,3TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	3861.4	Semi standard non polar	33892256
Glyburide,3TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	3911.7	Standard non polar	33892256
Glyburide,3TMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	4952.1	Standard polar	33892256
Glyburide,1TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C(C)(C)C	4504.3	Semi standard non polar	33892256
Glyburide,1TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C(C)(C)C	3699.0	Standard non polar	33892256
Glyburide,1TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1)[Si](C)(C)C(C)(C)C	5596.3	Standard polar	33892256
Glyburide,1TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	4413.0	Semi standard non polar	33892256
Glyburide,1TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	3703.8	Standard non polar	33892256
Glyburide,1TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	5536.7	Standard polar	33892256
Glyburide,1TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	4388.4	Semi standard non polar	33892256
Glyburide,1TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	3797.7	Standard non polar	33892256
Glyburide,1TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1	5462.1	Standard polar	33892256
Glyburide,2TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4505.3	Semi standard non polar	33892256
Glyburide,2TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4020.6	Standard non polar	33892256
Glyburide,2TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	5314.5	Standard polar	33892256
Glyburide,2TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4458.1	Semi standard non polar	33892256
Glyburide,2TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4104.9	Standard non polar	33892256
Glyburide,2TBDMS,isomer #2	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	5176.7	Standard polar	33892256
Glyburide,2TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4496.5	Semi standard non polar	33892256
Glyburide,2TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4187.6	Standard non polar	33892256
Glyburide,2TBDMS,isomer #3	COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	5130.9	Standard polar	33892256
Glyburide,3TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4599.6	Semi standard non polar	33892256
Glyburide,3TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4517.5	Standard non polar	33892256
Glyburide,3TBDMS,isomer #1	COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	4935.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glyburide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9755200000-129e50286730bac1e4e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glyburide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-qTof , Positive-QTOF	splash10-014i-0002190000-7f61119495ccea67ff2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-qTof , Positive-QTOF	splash10-00lu-0594000000-78579410f8f6799b400b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-qTof , Positive-QTOF	splash10-00lu-0594000000-78579410f8f6799b400b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-qTof , Positive-QTOF	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-QFT , negative-QTOF	splash10-00dl-0901300000-a19ba3565aec1b9acb36	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide , positive-QTOF	splash10-014i-0002290000-4a0641596c33a997d77e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide , positive-QTOF	splash10-014i-0319000000-b4fc8ec2ce4cb2f7b9fe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide , positive-QTOF	splash10-014i-0002190000-7f61119495ccea67ff2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide , positive-QTOF	splash10-014i-1629000000-bcf31c97391018018369	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide , positive-QTOF	splash10-014i-2911000000-7c5e8a23fd392fd3eb4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide LC-ESI-QFT , positive-QTOF	splash10-014i-0906000000-4ed189ce2c190cc04470	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 75V, Negative-QTOF	splash10-004i-3900000000-56a0233da7ea5ad5b008	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 15V, Positive-QTOF	splash10-014i-0009000000-e00bb352ba4f594be124	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 50V, Positive-QTOF	splash10-014i-0900000000-6741aab73ecc529efa18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 60V, Negative-QTOF	splash10-00b9-1900000000-4a4d0776263284e00e66	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 30V, Positive-QTOF	splash10-014i-0905000000-6ea41e91252175c31f91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 45V, Positive-QTOF	splash10-014i-0900000000-1b775c20ef2ec84ca78a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 40V, Positive-QTOF	splash10-014i-0911000000-0cdcc11d3b177ada89a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glyburide 30V, Positive-QTOF	splash10-014i-0819000000-1d1b54a277888408f46c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 10V, Positive-QTOF	splash10-00kf-2209600000-84e7b22a56916b121823	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 20V, Positive-QTOF	splash10-000t-8924000000-237d0276b5971a341e21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 40V, Positive-QTOF	splash10-05fv-9810000000-b29be4db2d87cad02005	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 10V, Negative-QTOF	splash10-0007-3106900000-b388d1114dc8cc9dbee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 20V, Negative-QTOF	splash10-0gc4-2319000000-f708bea7c586cde056b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyburide 40V, Negative-QTOF	splash10-000y-9602000000-bac81070100f10ae3ae5	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Glibenclamide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01016	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01016	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01016

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3368

KEGG Compound ID

C07022

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glibenclamide

METLIN ID

Not Available

PubChem Compound

3488

PDB ID

Not Available

ChEBI ID

5441

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82. [PubMed:16634115 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. ATP-binding cassette sub-family A member 1

General function:: Involved in ATP binding
Specific function:: cAMP-dependent and sulfonylurea-sensitive anion transporter. Key gatekeeper influencing intracellular cholesterol transport
Gene Name:: ABCA1
Uniprot ID:: O95477
Molecular weight:: 254299.9

References

Reddy ST, Hama S, Ng C, Grijalva V, Navab M, Fogelman AM: ATP-binding cassette transporter 1 participates in LDL oxidation by artery wall cells. Arterioscler Thromb Vasc Biol. 2002 Nov 1;22(11):1877-83. [PubMed:12426219 ]
Muhl H, Hofler S, Pfeilschifter J: Inhibition of lipopolysaccharide/ATP-induced release of interleukin-18 by KN-62 and glyburide. Eur J Pharmacol. 2003 Dec 15;482(1-3):325-8. [PubMed:14660039 ]
Agassandian M, Mathur SN, Zhou J, Field FJ, Mallampalli RK: Oxysterols trigger ABCA1-mediated basolateral surfactant efflux. Am J Respir Cell Mol Biol. 2004 Aug;31(2):227-33. Epub 2004 Mar 23. [PubMed:15039140 ]
Nieland TJ, Chroni A, Fitzgerald ML, Maliga Z, Zannis VI, Kirchhausen T, Krieger M: Cross-inhibition of SR-BI- and ABCA1-mediated cholesterol transport by the small molecules BLT-4 and glyburide. J Lipid Res. 2004 Jul;45(7):1256-65. Epub 2004 Apr 21. [PubMed:15102890 ]
Alder-Baerens N, Muller P, Pohl A, Korte T, Hamon Y, Chimini G, Pomorski T, Herrmann A: Headgroup-specific exposure of phospholipids in ABCA1-expressing cells. J Biol Chem. 2005 Jul 15;280(28):26321-9. Epub 2005 May 19. [PubMed:15905177 ]

Enzyme Details

5. Cystic fibrosis transmembrane conductance regulator

General function:: Involved in ATP binding
Specific function:: Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in epithelial cells by regulating the SLC4A7 transporter. Can inhibit the chloride channel activity of ANO1.
Gene Name:: CFTR
Uniprot ID:: P13569
Molecular weight:: 168139.895

References

Reddy MM, Quinton PM: Effect of anion transport blockers on CFTR in the human sweat duct. J Membr Biol. 2002 Sep 1;189(1):15-25. [PubMed:12202948 ]
Jiang J, Song Y, Bai C, Koller BH, Matthay MA, Verkman AS: Pleural surface fluorescence measurement of Na+ and Cl- transport across the air space-capillary barrier. J Appl Physiol (1985). 2003 Jan;94(1):343-52. Epub 2002 Aug 30. [PubMed:12391048 ]
Zhou Z, Hu S, Hwang TC: Probing an open CFTR pore with organic anion blockers. J Gen Physiol. 2002 Nov;120(5):647-62. [PubMed:12407077 ]
Larsen EH, Amstrup J, Willumsen NJ: Beta-adrenergic receptors couple to CFTR chloride channels of intercalated mitochondria-rich cells in the heterocellular toad skin epithelium. Biochim Biophys Acta. 2003 Dec 30;1618(2):140-52. [PubMed:14729151 ]
Lee SY, Lee CO: Inhibition of Na+-K+ pump and L-type Ca2+ channel by glibenclamide in Guinea pig ventricular myocytes. J Pharmacol Exp Ther. 2005 Jan;312(1):61-8. Epub 2004 Sep 13. [PubMed:15365090 ]

Enzyme Details

6. ATP-sensitive inward rectifier potassium channel 1

General function:: Involved in inward rectifier potassium channel activity
Specific function:: In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:: KCNJ1
Uniprot ID:: P48048
Molecular weight:: 44794.6

References

Pondugula SR, Raveendran NN, Ergonul Z, Deng Y, Chen J, Sanneman JD, Palmer LG, Marcus DC: Glucocorticoid regulation of genes in the amiloride-sensitive sodium transport pathway by semicircular canal duct epithelium of neonatal rat. Physiol Genomics. 2006 Jan 12;24(2):114-23. Epub 2005 Nov 1. [PubMed:16263802 ]
Lu M, Leng Q, Egan ME, Caplan MJ, Boulpaep EL, Giebisch GH, Hebert SC: CFTR is required for PKA-regulated ATP sensitivity of Kir1.1 potassium channels in mouse kidney. J Clin Invest. 2006 Mar;116(3):797-807. Epub 2006 Feb 9. [PubMed:16470247 ]

Enzyme Details

7. ATP-sensitive inward rectifier potassium channel 11

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium
Gene Name:: KCNJ11
Uniprot ID:: Q14654
Molecular weight:: 43540.4

References

Hambrock A, Loffler-Walz C, Quast U: Glibenclamide binding to sulphonylurea receptor subtypes: dependence on adenine nucleotides. Br J Pharmacol. 2002 Aug;136(7):995-1004. [PubMed:12145099 ]
Nielsen FE, Bodvarsdottir TB, Worsaae A, MacKay P, Stidsen CE, Boonen HC, Pridal L, Arkhammar PO, Wahl P, Ynddal L, Junager F, Dragsted N, Tagmose TM, Mogensen JP, Koch A, Treppendahl SP, Hansen JB: 6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells. J Med Chem. 2002 Sep 12;45(19):4171-87. [PubMed:12213059 ]
Gojkovic-Bukarica L, Hambrock A, Loffler-Walz C, Quast U, Russ U: Mg2+ sensitizes KATP channels to inhibition by DIDS: dependence on the sulphonylurea receptor subunit. Br J Pharmacol. 2002 Oct;137(4):429-40. [PubMed:12359624 ]
Ball AJ, McCluskey JT, Flatt PR, McClenaghan NH: Chronic exposure to tolbutamide and glibenclamide impairs insulin secretion but not transcription of K(ATP) channel components. Pharmacol Res. 2004 Jul;50(1):41-6. [PubMed:15082027 ]
Lim JG, Lee HY, Yun JE, Kim SP, Park JW, Suh SI, Jang BC, Cho CH, Bae JH, Kim SS, Han J, Park MJ, Song DK: Taurine block of cloned ATP-sensitive K+ channels with different sulfonylurea receptor subunits expressed in Xenopus laevis oocytes. Biochem Pharmacol. 2004 Sep 1;68(5):901-10. [PubMed:15294453 ]

Enzyme Details

8. G protein-activated inward rectifier potassium channel 4

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This potassium channel is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by external barium
Gene Name:: KCNJ5
Uniprot ID:: P48544
Molecular weight:: 47667.3

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

9. ATP-binding cassette sub-family C member 8

General function:: Involved in ATP binding
Specific function:: Putative subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release
Gene Name:: ABCC8
Uniprot ID:: Q09428
Molecular weight:: 177006.4

References

Dabrowski M, Ashcroft FM, Ashfield R, Lebrun P, Pirotte B, Egebjerg J, Bondo Hansen J, Wahl P: The novel diazoxide analog 3-isopropylamino-7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener. Diabetes. 2002 Jun;51(6):1896-906. [PubMed:12031979 ]
Hambrock A, Preisig-Muller R, Russ U, Piehl A, Hanley PJ, Ray J, Daut J, Quast U, Derst C: Four novel splice variants of sulfonylurea receptor 1. Am J Physiol Cell Physiol. 2002 Aug;283(2):C587-98. [PubMed:12107069 ]
Hambrock A, Loffler-Walz C, Quast U: Glibenclamide binding to sulphonylurea receptor subtypes: dependence on adenine nucleotides. Br J Pharmacol. 2002 Aug;136(7):995-1004. [PubMed:12145099 ]
Nielsen FE, Bodvarsdottir TB, Worsaae A, MacKay P, Stidsen CE, Boonen HC, Pridal L, Arkhammar PO, Wahl P, Ynddal L, Junager F, Dragsted N, Tagmose TM, Mogensen JP, Koch A, Treppendahl SP, Hansen JB: 6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells. J Med Chem. 2002 Sep 12;45(19):4171-87. [PubMed:12213059 ]
Babenko AP, Bryan J: SUR-dependent modulation of KATP channels by an N-terminal KIR6.2 peptide. Defining intersubunit gating interactions. J Biol Chem. 2002 Nov 15;277(46):43997-4004. Epub 2002 Sep 3. [PubMed:12213829 ]
Ueda K, Komine J, Matsuo M, Seino S, Amachi T: Cooperative binding of ATP and MgADP in the sulfonylurea receptor is modulated by glibenclamide. Proc Natl Acad Sci U S A. 1999 Feb 16;96(4):1268-72. [PubMed:9990013 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Gedeon C, Behravan J, Koren G, Piquette-Miller M: Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102. Epub 2006 Feb 3. [PubMed:16460798 ]
Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: The sulphonylurea glibenclamide inhibits multidrug resistance protein (MRP1) activity in human lung cancer cells. Br J Pharmacol. 2001 Feb;132(3):778-84. [PubMed:11159731 ]

Enzyme Details

2. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: The sulphonylurea glibenclamide inhibits multidrug resistance protein (MRP1) activity in human lung cancer cells. Br J Pharmacol. 2001 Feb;132(3):778-84. [PubMed:11159731 ]
Gedeon C, Behravan J, Koren G, Piquette-Miller M: Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102. Epub 2006 Feb 3. [PubMed:16460798 ]

Enzyme Details

3. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378 ]

Enzyme Details

4. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Gedeon C, Behravan J, Koren G, Piquette-Miller M: Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102. Epub 2006 Feb 3. [PubMed:16460798 ]

Enzyme Details

5. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Byrne JA, Strautnieks SS, Mieli-Vergani G, Higgins CF, Linton KJ, Thompson RJ: The human bile salt export pump: characterization of substrate specificity and identification of inhibitors. Gastroenterology. 2002 Nov;123(5):1649-58. [PubMed:12404239 ]
Kemp DC, Brouwer KL: Viability assessment in sandwich-cultured rat hepatocytes after xenobiotic exposure. Toxicol In Vitro. 2004 Dec;18(6):869-77. [PubMed:15465654 ]
Horikawa M, Kato Y, Tyson CA, Sugiyama Y: Potential cholestatic activity of various therapeutic agents assessed by bile canalicular membrane vesicles isolated from rats and humans. Drug Metab Pharmacokinet. 2003;18(1):16-22. [PubMed:15618715 ]
Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
Noe J, Hagenbuch B, Meier PJ, St-Pierre MV: Characterization of the mouse bile salt export pump overexpressed in the baculovirus system. Hepatology. 2001 May;33(5):1223-31. [PubMed:11343252 ]
Funk C, Pantze M, Jehle L, Ponelle C, Scheuermann G, Lazendic M, Gasser R: Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt export pump (Bsep) by troglitazone and troglitazone sulfate. Toxicology. 2001 Oct 5;167(1):83-98. [PubMed:11557132 ]
Stieger B, Fattinger K, Madon J, Kullak-Ublick GA, Meier PJ: Drug- and estrogen-induced cholestasis through inhibition of the hepatocellular bile salt export pump (Bsep) of rat liver. Gastroenterology. 2000 Feb;118(2):422-30. [PubMed:10648470 ]

Enzyme Details

6. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Golstein PE, Boom A, van Geffel J, Jacobs P, Masereel B, Beauwens R: P-glycoprotein inhibition by glibenclamide and related compounds. Pflugers Arch. 1999 Apr;437(5):652-60. [PubMed:10087141 ]

Enzyme Details

7. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Gedeon C, Behravan J, Koren G, Piquette-Miller M: Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102. Epub 2006 Feb 3. [PubMed:16460798 ]
Pollex EK, Anger G, Hutson J, Koren G, Piquette-Miller M: Breast cancer resistance protein (BCRP)-mediated glyburide transport: effect of the C421A/Q141K BCRP single-nucleotide polymorphism. Drug Metab Dispos. 2010 May;38(5):740-4. doi: 10.1124/dmd.109.030791. Epub 2010 Feb 16. [PubMed:20159988 ]

Enzyme Details

8. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Enzyme Details

9. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Sawada K, Terada T, Saito H, Hashimoto Y, Inui K: Effects of glibenclamide on glycylsarcosine transport by the rat peptide transporters PEPT1 and PEPT2. Br J Pharmacol. 1999 Nov;128(6):1159-64. [PubMed:10578127 ]

Enzyme Details

10. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Sawada K, Terada T, Saito H, Hashimoto Y, Inui K: Effects of glibenclamide on glycylsarcosine transport by the rat peptide transporters PEPT1 and PEPT2. Br J Pharmacol. 1999 Nov;128(6):1159-64. [PubMed:10578127 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for Glyburide (HMDB0015151)

MOL for HMDB0015151 (Glyburide)

3D MOL for HMDB0015151 (Glyburide)

3D SDF for HMDB0015151 (Glyburide)

3D-SDF for HMDB0015151 (Glyburide)

PDB for HMDB0015151 (Glyburide)

3D PDB for HMDB0015151 (Glyburide)

SMILES for HMDB0015151 (Glyburide)

INCHI for HMDB0015151 (Glyburide)

Structure for HMDB0015151 (Glyburide)

3D Structure for HMDB0015151 (Glyburide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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