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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:52 UTC

Update Date

2021-09-16 15:29:20 UTC

HMDB ID

HMDB0014027

Secondary Accession Numbers

HMDB14027

Metabolite Identification

Common Name

7-Hydroxygliclazide

Description

7-Hydroxygliclazide 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. 7-Hydroxygliclazide is a moderately basic compound (based on its pKa). 7-Hydroxygliclazide is a metabolite of Gliclazide. 7-Hydroxygliclazide is only found in individuals that have used or taken Gliclazide. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Structure

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

HMDB0014027
     RDKit          3D
7-Hydroxygliclazide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -7.5681    1.4598    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3345    0.6023    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    0.8348    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    0.0465    0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.0029    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487   -1.9932    0.0650 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2502   -2.2935    1.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7848   -3.2924   -0.6406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2558   -1.1794   -0.7376 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0223   -1.1717   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -1.7855    0.9592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.5102   -0.7823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3479   -0.5439   -0.1361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951   -1.1373   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -0.3028   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194   -0.5630    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070    0.7970    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1503    0.9638    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564    1.8204    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711    1.0678   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.8080    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.2442   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1842   -0.4448   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4088    0.7786   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5297    2.2192   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6840    1.9912    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    1.6498    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    0.2078    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592   -0.7071   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324   -0.0261   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.1614   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -1.1822   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172   -0.4066   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416   -1.1689    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -1.0783    1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7287    0.8865    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490    1.9055    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    2.7453    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    2.0741   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.5523   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.9557    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9758    1.5405   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -2.0769   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9997   -0.6347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 13  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

[NO NAME]
  Mrv0541 09021217592D          
Created with ChemWriter - http://chemwriter.com
 23 25  0  0  0  0            999 V2000
    3.3002   -0.3808    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503   -0.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0147    0.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5857   -0.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7753   -1.8098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503   -1.8098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127   -1.0953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0449   -1.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0449   -2.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8257   -1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8257   -2.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -2.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3072   -1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -1.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877    1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    2.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1322   -1.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  7  1  0  0  0  0
  1 16  1  0  0  0  0
  2 15  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 15  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 14  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 14 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014027

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC(O)CC2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N3O4S/c1-10-2-4-14(5-3-10)23(21,22)17-15(20)16-18-8-11-6-13(19)7-12(11)9-18/h2-5,11-13,19H,6-9H2,1H3,(H2,16,17,20)

> <INCHI_KEY>
JMHDCYDSYHLATB-UHFFFAOYSA-N

> <FORMULA>
C15H21N3O4S

> <MOLECULAR_WEIGHT>
339.41

> <EXACT_MASS>
339.125276865

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.04787212100679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{5-hydroxy-octahydrocyclopenta[c]pyrrol-2-yl}-1-(4-methylbenzenesulfonyl)urea

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.3469225586666662

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.028736958040675

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.069305750618991

> <JCHEM_PKA_STRONGEST_BASIC>
1.0209922167260628

> <JCHEM_POLAR_SURFACE_AREA>
98.74000000000001

> <JCHEM_REFRACTIVITY>
85.54560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{5-hydroxy-hexahydro-1H-cyclopenta[c]pyrrol-2-yl}-1-(4-methylbenzenesulfonyl)urea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014027
     RDKit          3D
7-Hydroxygliclazide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -7.5681    1.4598    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3345    0.6023    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    0.8348    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    0.0465    0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.0029    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487   -1.9932    0.0650 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2502   -2.2935    1.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7848   -3.2924   -0.6406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2558   -1.1794   -0.7376 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0223   -1.1717   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -1.7855    0.9592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.5102   -0.7823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3479   -0.5439   -0.1361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951   -1.1373   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -0.3028   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194   -0.5630    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070    0.7970    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1503    0.9638    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564    1.8204    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711    1.0678   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.8080    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.2442   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1842   -0.4448   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4088    0.7786   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5297    2.2192   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6840    1.9912    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    1.6498    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    0.2078    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592   -0.7071   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324   -0.0261   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.1614   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -1.1822   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172   -0.4066   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416   -1.1689    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -1.0783    1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7287    0.8865    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490    1.9055    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    2.7453    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    2.0741   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.5523   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.9557    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9758    1.5405   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -2.0769   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9997   -0.6347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 13  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 02-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-12         0                                  
HETATM    1  S   UNK     0       6.160  -0.711   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.241  -0.711   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.494   0.059   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.827  -1.481   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.781  -3.378   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.241  -3.378   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.930  -2.045   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.150  -2.608   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.150  -4.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.608  -2.139   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.608  -4.618   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.686  -2.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.686  -4.624   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.507  -3.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.471  -2.045   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.390   0.623   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.160   1.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.850   0.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.850   3.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.390   3.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   1.957   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   4.624   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      17.047  -3.378   0.000  0.00  0.00           O+0
CONECT    1    3    4    7   16                                             
CONECT    2   15                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    6   12   13                                                  
CONECT    6    5   15                                                       
CONECT    7    1   15                                                       
CONECT    8    9   10   12                                                  
CONECT    9    8   11   13                                                  
CONECT   10    8   14                                                       
CONECT   11    9   14                                                       
CONECT   12    5    8                                                       
CONECT   13    5    9                                                       
CONECT   14   10   11   23                                                  
CONECT   15    2    6    7                                                  
CONECT   16    1   17   18                                                  
CONECT   17   16   20                                                       
CONECT   18   16   21                                                       
CONECT   19   20   21   22                                                  
CONECT   20   17   19                                                       
CONECT   21   18   19                                                       
CONECT   22   19                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0014027
HETATM    1  C1  UNL     1      -7.568   1.460   0.039  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.335   0.602   0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.301   0.835   0.919  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.170   0.046   0.908  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.014  -1.003   0.024  1.00  0.00           C  
HETATM    6  S1  UNL     1      -2.549  -1.993   0.065  1.00  0.00           S  
HETATM    7  O1  UNL     1      -2.250  -2.294   1.497  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.785  -3.292  -0.641  1.00  0.00           O  
HETATM    9  N1  UNL     1      -1.256  -1.179  -0.738  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.022  -1.172  -0.154  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.168  -1.786   0.959  1.00  0.00           O  
HETATM   12  N2  UNL     1       1.094  -0.510  -0.782  1.00  0.00           N  
HETATM   13  N3  UNL     1       2.348  -0.544  -0.136  1.00  0.00           N  
HETATM   14  C7  UNL     1       3.295  -1.137  -1.053  1.00  0.00           C  
HETATM   15  C8  UNL     1       4.558  -0.303  -0.933  1.00  0.00           C  
HETATM   16  C9  UNL     1       5.219  -0.563   0.406  1.00  0.00           C  
HETATM   17  C10 UNL     1       5.607   0.797   0.951  1.00  0.00           C  
HETATM   18  O4  UNL     1       5.150   0.964   2.244  1.00  0.00           O  
HETATM   19  C11 UNL     1       5.056   1.820   0.002  1.00  0.00           C  
HETATM   20  C12 UNL     1       3.971   1.068  -0.732  1.00  0.00           C  
HETATM   21  C13 UNL     1       2.756   0.808   0.093  1.00  0.00           C  
HETATM   22  C14 UNL     1      -5.039  -1.244  -0.862  1.00  0.00           C  
HETATM   23  C15 UNL     1      -6.184  -0.445  -0.849  1.00  0.00           C  
HETATM   24  H1  UNL     1      -8.409   0.779  -0.216  1.00  0.00           H  
HETATM   25  H2  UNL     1      -7.530   2.219  -0.782  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.684   1.991   0.992  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.397   1.650   1.622  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.330   0.208   1.596  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.459  -0.707  -1.639  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.932  -0.026  -1.684  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.506  -2.161  -0.705  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.916  -1.182  -2.072  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.217  -0.407  -1.791  1.00  0.00           H  
HETATM   34  H11 UNL     1       6.142  -1.169   0.254  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.528  -1.078   1.098  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.729   0.887   0.970  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.849   1.906   2.315  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.704   2.745   0.478  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.833   2.074  -0.741  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.692   1.552  -1.695  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.919   0.956   1.176  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.976   1.541  -0.238  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.929  -2.077  -1.564  1.00  0.00           H  
HETATM   44  H21 UNL     1      -7.000  -0.635  -1.549  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   23
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   22
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   29
CONECT   10   11   11   12
CONECT   12   13   30
CONECT   13   14   21
CONECT   14   15   31   32
CONECT   15   16   20   33
CONECT   16   17   34   35
CONECT   17   18   19   36
CONECT   18   37
CONECT   19   20   38   39
CONECT   20   21   40
CONECT   21   41   42
CONECT   22   23   23   43
CONECT   23   44
END

HMDB0014027
     RDKit          3D
7-Hydroxygliclazide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -7.5681    1.4598    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3345    0.6023    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3012    0.8348    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    0.0465    0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -1.0029    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487   -1.9932    0.0650 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2502   -2.2935    1.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7848   -3.2924   -0.6406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2558   -1.1794   -0.7376 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0223   -1.1717   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -1.7855    0.9592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.5102   -0.7823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3479   -0.5439   -0.1361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951   -1.1373   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -0.3028   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194   -0.5630    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070    0.7970    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1503    0.9638    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564    1.8204    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711    1.0678   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.8080    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.2442   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1842   -0.4448   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4088    0.7786   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5297    2.2192   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6840    1.9912    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    1.6498    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    0.2078    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592   -0.7071   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324   -0.0261   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.1614   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156   -1.1822   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172   -0.4066   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416   -1.1689    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -1.0783    1.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7287    0.8865    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490    1.9055    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    2.7453    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8328    2.0741   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.5523   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.9557    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9758    1.5405   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290   -2.0769   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9997   -0.6347   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
  5 22  1  0
 22 23  2  0
 23  2  1  0
 21 13  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N'-{5-hydroxy-octahydrocyclopenta[c]pyrrol-2-yl}-N-(4-methylbenzenesulfonyl)carbamimidate	Generator
N'-{5-hydroxy-octahydrocyclopenta[c]pyrrol-2-yl}-N-(4-methylbenzenesulphonyl)carbamimidate	Generator
N'-{5-hydroxy-octahydrocyclopenta[c]pyrrol-2-yl}-N-(4-methylbenzenesulphonyl)carbamimidic acid	Generator

Chemical Formula

C₁₅H₂₁N₃O₄S

Average Molecular Weight

339.41

Monoisotopic Molecular Weight

339.125276865

IUPAC Name

3-{5-hydroxy-octahydrocyclopenta[c]pyrrol-2-yl}-1-(4-methylbenzenesulfonyl)urea

Traditional Name

3-{5-hydroxy-hexahydro-1H-cyclopenta[c]pyrrol-2-yl}-1-(4-methylbenzenesulfonyl)urea

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC(O)CC2C1

InChI Identifier

InChI=1S/C15H21N3O4S/c1-10-2-4-14(5-3-10)23(21,22)17-15(20)16-18-8-11-6-13(19)7-12(11)9-18/h2-5,11-13,19H,6-9H2,1H3,(H2,16,17,20)

InChI Key

JMHDCYDSYHLATB-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
Tosyl compound
Benzenesulfonyl group
Toluene
Sulfonylurea
Cyclic alcohol
Pyrrolidine
Semicarbazide
Organic sulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Carbonic acid derivative
Secondary alcohol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	0.34	ALOGPS
logP	0.35	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	1.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.55 m³·mol⁻¹	ChemAxon
Polarizability	35.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.428	31661259
DarkChem	[M-H]-	175.296	31661259
DeepCCS	[M+H]+	171.642	30932474
DeepCCS	[M-H]-	169.284	30932474
DeepCCS	[M-2H]-	202.961	30932474
DeepCCS	[M+Na]+	178.188	30932474
AllCCS	[M+H]+	179.6	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	175.9	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	176.2	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.	4.47 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6209 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1036.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	210.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	330.0 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	373.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	409.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	706.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	329.3 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	1210.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.2 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	229.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxygliclazide	CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC(O)CC2C1	4040.4	Standard polar	33892256
7-Hydroxygliclazide	CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC(O)CC2C1	2079.0	Standard non polar	33892256
7-Hydroxygliclazide	CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CC(O)CC2C1	3000.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxygliclazide,1TMS,isomer #1	CC1=CC=C(S(=O)(=O)NC(=O)NN2CC3CC(O[Si](C)(C)C)CC3C2)C=C1	3071.9	Semi standard non polar	33892256
7-Hydroxygliclazide,1TMS,isomer #2	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O)CC3C2)[Si](C)(C)C)C=C1	2979.8	Semi standard non polar	33892256
7-Hydroxygliclazide,1TMS,isomer #3	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C)C=C1	2966.2	Semi standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	2945.0	Semi standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	2919.4	Standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	4098.8	Standard polar	33892256
7-Hydroxygliclazide,2TMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	2939.0	Semi standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	2955.1	Standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)C=C1	4014.5	Standard polar	33892256
7-Hydroxygliclazide,2TMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	2897.4	Semi standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3099.9	Standard non polar	33892256
7-Hydroxygliclazide,2TMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	4107.6	Standard polar	33892256
7-Hydroxygliclazide,3TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	2895.7	Semi standard non polar	33892256
7-Hydroxygliclazide,3TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3128.7	Standard non polar	33892256
7-Hydroxygliclazide,3TMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C)CC3C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3782.4	Standard polar	33892256
7-Hydroxygliclazide,1TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)NC(=O)NN2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)C=C1	3322.0	Semi standard non polar	33892256
7-Hydroxygliclazide,1TBDMS,isomer #2	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3254.9	Semi standard non polar	33892256
7-Hydroxygliclazide,1TBDMS,isomer #3	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3245.9	Semi standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3455.4	Semi standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3405.4	Standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)NN2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	4142.2	Standard polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3426.3	Semi standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	3464.8	Standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #2	CC1=CC=C(S(=O)(=O)NC(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)C=C1	4031.2	Standard polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3442.5	Semi standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3599.8	Standard non polar	33892256
7-Hydroxygliclazide,2TBDMS,isomer #3	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4100.6	Standard polar	33892256
7-Hydroxygliclazide,3TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3648.8	Semi standard non polar	33892256
7-Hydroxygliclazide,3TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3869.0	Standard non polar	33892256
7-Hydroxygliclazide,3TBDMS,isomer #1	CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CC3CC(O[Si](C)(C)C(C)(C)C)CC3C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3863.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxygliclazide GC-MS (Non-derivatized) - 70eV, Positive	splash10-008c-9774000000-8f724efc313ac06d86d9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxygliclazide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9304000000-3436c9e9e6fd8fd7f313	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxygliclazide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 10V, Positive-QTOF	splash10-00dl-0709000000-8c9535def8ed00ac5b56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 20V, Positive-QTOF	splash10-05i3-0900000000-e8a0757cc82cf776857a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 40V, Positive-QTOF	splash10-0fi0-9600000000-b20a52c4b57786f735b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 10V, Negative-QTOF	splash10-0079-0819000000-17712c4ca61a3cfed032	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 20V, Negative-QTOF	splash10-00dm-1900000000-c6595091321b61b8c1ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 40V, Negative-QTOF	splash10-00bc-8900000000-6e0f80a448ca31a802ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 10V, Positive-QTOF	splash10-0006-0409000000-a27d6e2e230d7eb66f69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 20V, Positive-QTOF	splash10-0006-6916000000-3b6ec609e9cadd5719cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 40V, Positive-QTOF	splash10-0006-9410000000-bd330ce295cbd4f6f1c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 10V, Negative-QTOF	splash10-000i-0109000000-34ad116c91da863db24b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 20V, Negative-QTOF	splash10-00di-1912000000-ba42435003deb49080d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxygliclazide 40V, Negative-QTOF	splash10-00di-5900000000-96565a3a22a17e00044f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Gliclazide 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	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750725

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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 ]

Enzyme Details

2. 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

3. Vascular endothelial growth factor A

General function:: Involved in growth factor activity
Specific function:: Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activate downstream signaling pathways, does not activate angiogenesis and inhibits tumor growth
Gene Name:: VEGFA
Uniprot ID:: P15692
Molecular weight:: 27042.2

References

Mamputu JC, Renier G: Advanced glycation end products increase, through a protein kinase C-dependent pathway, vascular endothelial growth factor expression in retinal endothelial cells. Inhibitory effect of gliclazide. J Diabetes Complications. 2002 Jul-Aug;16(4):284-93. [PubMed:12126787 ]
Mamputu JC, Renier G: Signalling pathways involved in retinal endothelial cell proliferation induced by advanced glycation end products: inhibitory effect of gliclazide. Diabetes Obes Metab. 2004 Mar;6(2):95-103. [PubMed:14746574 ]
Li L, Renier G: Activation of nicotinamide adenine dinucleotide phosphate (reduced form) oxidase by advanced glycation end products links oxidative stress to altered retinal vascular endothelial growth factor expression. Metabolism. 2006 Nov;55(11):1516-23. [PubMed:17046555 ]
Kimura T, Takagi H, Suzuma K, Kita M, Watanabe D, Yoshimura N: Comparisons between the beneficial effects of different sulphonylurea treatments on ischemia-induced retinal neovascularization. Free Radic Biol Med. 2007 Aug 1;43(3):454-61. Epub 2007 May 3. [PubMed:17602961 ]

Enzyme Details

4. 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

Gribble FM, Ashcroft FM: Sulfonylurea sensitivity of adenosine triphosphate-sensitive potassium channels from beta cells and extrapancreatic tissues. Metabolism. 2000 Oct;49(10 Suppl 2):3-6. [PubMed:11078468 ]
Harrower A: Gliclazide modified release: from once-daily administration to 24-hour blood glucose control. Metabolism. 2000 Oct;49(10 Suppl 2):7-11. [PubMed:11078469 ]
Lawrence CL, Proks P, Rodrigo GC, Jones P, Hayabuchi Y, Standen NB, Ashcroft FM: Gliclazide produces high-affinity block of KATP channels in mouse isolated pancreatic beta cells but not rat heart or arterial smooth muscle cells. Diabetologia. 2001 Aug;44(8):1019-25. [PubMed:11484080 ]
Reimann F, Ashcroft FM, Gribble FM: Structural basis for the interference between nicorandil and sulfonylurea action. Diabetes. 2001 Oct;50(10):2253-9. [PubMed:11574406 ]
Proks P, Reimann F, Green N, Gribble F, Ashcroft F: Sulfonylurea stimulation of insulin secretion. Diabetes. 2002 Dec;51 Suppl 3:S368-76. [PubMed:12475777 ]

Showing metabocard for 7-Hydroxygliclazide (HMDB0014027)

MOL for HMDB0014027 (7-Hydroxygliclazide)

3D MOL for HMDB0014027 (7-Hydroxygliclazide)

3D SDF for HMDB0014027 (7-Hydroxygliclazide)

3D-SDF for HMDB0014027 (7-Hydroxygliclazide)

PDB for HMDB0014027 (7-Hydroxygliclazide)

3D PDB for HMDB0014027 (7-Hydroxygliclazide)

SMILES for HMDB0014027 (7-Hydroxygliclazide)

INCHI for HMDB0014027 (7-Hydroxygliclazide)

Structure for HMDB0014027 (7-Hydroxygliclazide)

3D Structure for HMDB0014027 (7-Hydroxygliclazide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References