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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (1) Show 10 proteins XML

enzymes (9)transporters (1) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014545

Secondary Accession Numbers

HMDB14545

Metabolite Identification

Common Name

Nisoldipine

Description

Nisoldipine is a 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nisoldipine prevents calcium-dependent smooth muscle contraction and subsequent vasoconstriction. Nisoldipine may be used in alone or in combination with other agents in the management of hypertension.

Structure

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

401
  Mrv0541 02231214392D          

 28 29  0  0  1  0            999 V2000
    3.7935   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.3183    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.0804    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4933    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 22  1  0  0  0  0
  2 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 15  2  0  0  0  0
  4 19  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 16 23  2  0  0  0  0
 17 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 21 27  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  2  0  0  0  0
M  CHG  2   5  -1   8   1
M  END

HMDB0014545
     RDKit          3D
Nisoldipine
 52 53  0  0  0  0  0  0  0  0999 V2000
   -5.2331    0.4626    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849    0.0700    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.2011    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.9711   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -1.5689    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015   -2.7939   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.7406   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391   -3.2093   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -2.2861    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -2.7539    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -1.0629    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.1493    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189    1.0061    1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -0.4784    0.8851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044    0.1951    1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    1.3089    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    2.4752    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.8242   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385   -0.6102    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273    0.7965    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822    1.6256    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    2.9620    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426    3.5462   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    2.7767   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.3975   -0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.7427   -2.0605 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.9366    1.1773   -3.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -0.3119   -2.0868 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4397    0.9350   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286   -0.3877    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3893    1.1767    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3908   -3.9900    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -4.7227   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394   -3.4933   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -4.2070   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756   -2.2120   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -3.8165   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936   -2.7522    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.5391    2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -0.5511    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    1.7398    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5915    2.2933   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0196    3.3385   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686    2.7929    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6919    0.2280   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721    0.1891   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704    1.7233   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.6727    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352    1.2209    2.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688    3.5827    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239    4.5953   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    3.2215   -2.0646 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 19  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
M  CHG  2  26   1  28  -1
M  END

401
  Mrv0541 02231214392D          

 28 29  0  0  1  0            999 V2000
    3.7935   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.3183    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.0804    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4933    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 22  1  0  0  0  0
  2 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 15  2  0  0  0  0
  4 19  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 16 23  2  0  0  0  0
 17 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 21 27  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  2  0  0  0  0
M  CHG  2   5  -1   8   1
M  END
> <DATABASE_ID>
HMDB0014545

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3

> <INCHI_KEY>
VKQFCGNPDRICFG-UHFFFAOYSA-N

> <FORMULA>
C20H24N2O6

> <MOLECULAR_WEIGHT>
388.4144

> <EXACT_MASS>
388.16343651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.719138737253246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.059797457666667

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.3193070614228155

> <JCHEM_POLAR_SURFACE_AREA>
110.45000000000002

> <JCHEM_REFRACTIVITY>
105.90890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nisoldipine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014545
     RDKit          3D
Nisoldipine
 52 53  0  0  0  0  0  0  0  0999 V2000
   -5.2331    0.4626    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849    0.0700    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.2011    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.9711   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -1.5689    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015   -2.7939   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.7406   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391   -3.2093   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -2.2861    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -2.7539    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -1.0629    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.1493    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189    1.0061    1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -0.4784    0.8851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044    0.1951    1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    1.3089    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    2.4752    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.8242   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385   -0.6102    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273    0.7965    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822    1.6256    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    2.9620    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426    3.5462   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    2.7767   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.3975   -0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.7427   -2.0605 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.9366    1.1773   -3.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -0.3119   -2.0868 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4397    0.9350   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286   -0.3877    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3893    1.1767    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3908   -3.9900    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -4.7227   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394   -3.4933   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -4.2070   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756   -2.2120   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -3.8165   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936   -2.7522    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.5391    2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -0.5511    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    1.7398    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5915    2.2933   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0196    3.3385   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686    2.7929    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6919    0.2280   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721    0.1891   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704    1.7233   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.6727    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352    1.2209    2.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688    3.5827    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239    4.5953   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    3.2215   -2.0646 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 19  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
M  CHG  2  26   1  28  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 401                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081  -1.063   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.083  -1.063   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   1.247   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.750   1.247   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.750   4.327   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0      15.083   2.017   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      11.082  -3.373   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      13.750   2.787   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      11.082  -0.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -1.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -1.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -2.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416  -2.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -0.293   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.416   2.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   2.017   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -3.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750  -0.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.750  -3.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -1.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.748  -0.293   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.416   3.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748   3.557   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.082   4.327   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -0.293   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414  -2.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.417  -0.293   0.000  0.00  0.00           C+0
CONECT    1   15   22                                                       
CONECT    2   19   28                                                       
CONECT    3   15                                                            
CONECT    4   19                                                            
CONECT    5    8                                                            
CONECT    6    8                                                            
CONECT    7   13   14                                                       
CONECT    8    5    6   16                                                  
CONECT    9   10   11   12                                                  
CONECT   10    9   13   15                                                  
CONECT   11    9   14   19                                                  
CONECT   12    9   16   17                                                  
CONECT   13    7   10   18                                                  
CONECT   14    7   11   20                                                  
CONECT   15    1    3   10                                                  
CONECT   16    8   12   23                                                  
CONECT   17   12   24                                                       
CONECT   18   13                                                            
CONECT   19    2    4   11                                                  
CONECT   20   14                                                            
CONECT   21   22   26   27                                                  
CONECT   22    1   21                                                       
CONECT   23   16   25                                                       
CONECT   24   17   25                                                       
CONECT   25   23   24                                                       
CONECT   26   21                                                            
CONECT   27   21                                                            
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0014545
HETATM    1  C1  UNL     1      -5.233   0.463   0.355  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.885   0.070   0.408  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.446  -1.201   0.047  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.365  -1.971  -0.334  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.048  -1.569   0.115  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.701  -2.794  -0.244  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.730  -3.741  -0.693  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.339  -3.209  -0.249  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.655  -2.286   0.136  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.084  -2.754   0.117  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.342  -1.063   0.498  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.441  -0.149   0.880  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.119   1.006   1.220  1.00  0.00           O  
HETATM   14  O4  UNL     1       2.750  -0.478   0.885  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.904   0.195   1.182  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.312   1.309   0.304  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.383   2.475   0.184  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.761   0.824  -1.075  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.039  -0.610   0.618  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.327   0.796   0.281  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.882   1.626   1.277  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.138   2.962   1.105  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.843   3.546  -0.106  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.304   2.777  -1.100  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.041   1.398  -0.920  1.00  0.00           C  
HETATM   26  N2  UNL     1      -0.560   0.743  -2.061  1.00  0.00           N1+
HETATM   27  O5  UNL     1      -0.937   1.177  -3.196  1.00  0.00           O  
HETATM   28  O6  UNL     1       0.246  -0.312  -2.087  1.00  0.00           O1-
HETATM   29  H1  UNL     1      -5.440   0.935  -0.621  1.00  0.00           H  
HETATM   30  H2  UNL     1      -5.929  -0.388   0.573  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.389   1.177   1.213  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.391  -3.990   0.163  1.00  0.00           H  
HETATM   33  H5  UNL     1      -2.214  -4.723  -0.918  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.239  -3.493  -1.629  1.00  0.00           H  
HETATM   35  H7  UNL     1      -0.088  -4.207  -0.542  1.00  0.00           H  
HETATM   36  H8  UNL     1       2.676  -2.212  -0.627  1.00  0.00           H  
HETATM   37  H9  UNL     1       2.073  -3.816  -0.191  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.494  -2.752   1.146  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.932   0.539   2.264  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.762  -0.551   1.171  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.271   1.740   0.752  1.00  0.00           H  
HETATM   42  H14 UNL     1       2.591   2.293  -0.559  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.020   3.339  -0.218  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.069   2.793   1.177  1.00  0.00           H  
HETATM   45  H17 UNL     1       5.692   0.228  -1.018  1.00  0.00           H  
HETATM   46  H18 UNL     1       3.972   0.189  -1.545  1.00  0.00           H  
HETATM   47  H19 UNL     1       4.970   1.723  -1.684  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.221  -0.673   1.765  1.00  0.00           H  
HETATM   49  H21 UNL     1      -2.135   1.221   2.247  1.00  0.00           H  
HETATM   50  H22 UNL     1      -2.569   3.583   1.893  1.00  0.00           H  
HETATM   51  H23 UNL     1      -2.024   4.595  -0.294  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.062   3.222  -2.065  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   19
CONECT    6    7    8
CONECT    7   32   33   34
CONECT    8    9   35
CONECT    9   10   11   11
CONECT   10   36   37   38
CONECT   11   12   19
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   39   40
CONECT   16   17   18   41
CONECT   17   42   43   44
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   21   25
CONECT   21   22   49
CONECT   22   23   23   50
CONECT   23   24   51
CONECT   24   25   25   52
CONECT   25   26
CONECT   26   27   27   28
END

HMDB0014545
     RDKit          3D
Nisoldipine
 52 53  0  0  0  0  0  0  0  0999 V2000
   -5.2331    0.4626    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849    0.0700    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.2011    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3654   -1.9711   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -1.5689    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015   -2.7939   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -3.7406   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391   -3.2093   -0.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -2.2861    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -2.7539    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -1.0629    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.1493    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189    1.0061    1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -0.4784    0.8851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044    0.1951    1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    1.3089    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    2.4752    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.8242   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385   -0.6102    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273    0.7965    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822    1.6256    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    2.9620    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426    3.5462   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    2.7767   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411    1.3975   -0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.7427   -2.0605 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.9366    1.1773   -3.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -0.3119   -2.0868 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.4397    0.9350   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286   -0.3877    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3893    1.1767    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3908   -3.9900    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -4.7227   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2394   -3.4933   -1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -4.2070   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756   -2.2120   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -3.8165   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936   -2.7522    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    0.5391    2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -0.5511    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    1.7398    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5915    2.2933   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0196    3.3385   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686    2.7929    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6919    0.2280   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721    0.1891   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704    1.7233   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.6727    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352    1.2209    2.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688    3.5827    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239    4.5953   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    3.2215   -2.0646 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 19  5  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
M  CHG  2  26   1  28  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sular	Kegg
Nisoldipin	HMDB
Bay K 5552	HMDB

Chemical Formula

C₂₀H₂₄N₂O₆

Average Molecular Weight

388.4144

Monoisotopic Molecular Weight

388.16343651

IUPAC Name

3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Traditional Name

nisoldipine

CAS Registry Number

63675-72-9

SMILES

COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C

InChI Identifier

InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3

InChI Key

VKQFCGNPDRICFG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Dihydropyridinecarboxylic acid derivative
Nitrobenzene
Nitroaromatic compound
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Organic nitro compound
Carboxylic acid ester
C-nitro compound
Amino acid or derivatives
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Allyl-type 1,3-dipolar organic compound
Secondary aliphatic amine
Enamine
Organic oxoazanium
Secondary amine
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:76917 )
diester (CHEBI:76917 )
methyl ester (CHEBI:76917 )
dihydropyridine (CHEBI:76917 )

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

Membrane (HMDB: HMDB0014545)

Source

Exogenous

Exogenous (HMDB: HMDB0014545)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nisoldipine Action Pathway (PathBank: SMP0000381)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0058 g/L	Not Available
LogP	3.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	187.231	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001067

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0058 g/L	ALOGPS
logP	3.63	ALOGPS
logP	3.06	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	5.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	105.91 m³·mol⁻¹	ChemAxon
Polarizability	39.72 Å³	ChemAxon
Number of Rings	2	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]+	190.97	31661259
DarkChem	[M-H]-	190.248	31661259
DeepCCS	[M+H]+	192.481	30932474
DeepCCS	[M-H]-	189.221	30932474
DeepCCS	[M-2H]-	223.967	30932474
DeepCCS	[M+Na]+	200.135	30932474
AllCCS	[M+H]+	190.3	32859911
AllCCS	[M+H-H2O]+	187.6	32859911
AllCCS	[M+NH4]+	192.8	32859911
AllCCS	[M+Na]+	193.5	32859911
AllCCS	[M-H]-	195.2	32859911
AllCCS	[M+Na-2H]-	195.6	32859911
AllCCS	[M+HCOO]-	196.2	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.	8.2 minutes	32390414
Predicted by Siyang on May 30, 2022	17.0252 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2854.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	381.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	541.3 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	806.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1296.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	649.8 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	1839.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	468.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	258.6 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	36.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nisoldipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C	3919.7	Standard polar	33892256
Nisoldipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C	2642.7	Standard non polar	33892256
Nisoldipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C	2857.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nisoldipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	2688.4	Semi standard non polar	33892256
Nisoldipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	2476.0	Standard non polar	33892256
Nisoldipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	3610.2	Standard polar	33892256
Nisoldipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	2944.0	Semi standard non polar	33892256
Nisoldipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	2721.9	Standard non polar	33892256
Nisoldipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+](=O)[O-]	3622.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nisoldipine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-5059000000-15c76c3553190c789d84	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nisoldipine 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 - Nisoldipine 10V, Positive-QTOF	splash10-052r-7009000000-41eddaf4853ac4a37e28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 20V, Positive-QTOF	splash10-0a4i-9004000000-c2d757da92039c3c78eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 40V, Positive-QTOF	splash10-0a4i-9000000000-e8dce16b1cdb4e9e030b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 10V, Negative-QTOF	splash10-000i-1009000000-44a09fee0814fad6e0a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 20V, Negative-QTOF	splash10-000i-3009000000-23e42ff91501270026ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 40V, Negative-QTOF	splash10-0ab9-9044000000-ba0fba52523b1d58d5a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 10V, Negative-QTOF	splash10-000i-0009000000-8fe78917ea0af1c8457f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 20V, Negative-QTOF	splash10-00kr-0039000000-050b9d500d2bb8bbf4dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 40V, Negative-QTOF	splash10-0002-9030000000-f84f085e200cfb6a746a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 10V, Positive-QTOF	splash10-00kr-0009000000-cba054bd2270a25fdb3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 20V, Positive-QTOF	splash10-00kr-0196000000-f5d5e228cc14d59c4ad1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nisoldipine 40V, Positive-QTOF	splash10-0006-2391000000-f0788a183fed36d34d93	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nisoldipine 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 DB00401	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00401	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00401

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4343

KEGG Compound ID

C07699

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nisoldipine

METLIN ID

Not Available

PubChem Compound

4499

PDB ID

Not Available

ChEBI ID

76917

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

Hamilton SF, Houle LM, Thadani U: Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure. Heart Dis. 1999 Nov-Dec;1(5):279-88. [PubMed:11720635 ]
Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF: Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. Epub 2003 Oct 6. [PubMed:14530219 ]
Mielcarek J, Grobelny P, Szamburska O: The effect of beta-carotene on the photostability of nisoldipine. Methods Find Exp Clin Pharmacol. 2005 Apr;27(3):167-71. [PubMed:15834448 ]

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

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 3A5

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.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

3. Cytochrome P450 3A7

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.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

4. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

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

5. Voltage-dependent L-type calcium channel subunit alpha-1D

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1D gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:: CACNA1D
Uniprot ID:: Q01668
Molecular weight:: 245138.8

References

Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J: Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. Mol Pharmacol. 2009 Feb;75(2):407-14. doi: 10.1124/mol.108.049981. Epub 2008 Nov 24. [PubMed:19029287 ]

Enzyme Details

6. Voltage-dependent L-type calcium channel subunit alpha-1C

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
Gene Name:: CACNA1C
Uniprot ID:: Q13936
Molecular weight:: 248974.1

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hu H, Marban E: Isoform-specific inhibition of L-type calcium channels by dihydropyridines is independent of isoform-specific gating properties. Mol Pharmacol. 1998 May;53(5):902-7. [PubMed:9584217 ]
Morel N, Buryi V, Feron O, Gomez JP, Christen MO, Godfraind T: The action of calcium channel blockers on recombinant L-type calcium channel alpha1-subunits. Br J Pharmacol. 1998 Nov;125(5):1005-12. [PubMed:9846638 ]
Wei X, Pan S, Lang W, Kim H, Schneider T, Perez-Reyes E, Birnbaumer L: Molecular determinants of cardiac Ca2+ channel pharmacology. Subunit requirement for the high affinity and allosteric regulation of dihydropyridine binding. J Biol Chem. 1995 Nov 10;270(45):27106-11. [PubMed:7592963 ]

Enzyme Details

7. Voltage-dependent calcium channel subunit alpha-2/delta-1

General function:: Involved in metal ion binding
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling
Gene Name:: CACNA2D1
Uniprot ID:: P54289
Molecular weight:: 124566.9

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

8. Voltage-dependent L-type calcium channel subunit alpha-1S

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1S gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1S subunit play an important role in excitation-contraction coupling in skeletal muscle
Gene Name:: CACNA1S
Uniprot ID:: Q13698
Molecular weight:: 212348.1

References

Peterson BZ, Catterall WA: Allosteric interactions required for high-affinity binding of dihydropyridine antagonists to Ca(V)1.1 Channels are modulated by calcium in the pore. Mol Pharmacol. 2006 Aug;70(2):667-75. Epub 2006 May 4. [PubMed:16675661 ]

Enzyme Details

9. Voltage-dependent L-type calcium channel subunit beta-2

General function:: Involved in voltage-gated calcium channel activity
Specific function:: The beta subunit of voltage-dependent calcium channels contributes to the function of the calcium channel by increasing peak calcium current, shifting the voltage dependencies of activation and inactivation, modulating G protein inhibition and controlling the alpha-1 subunit membrane targeting
Gene Name:: CACNB2
Uniprot ID:: Q08289
Molecular weight:: 73579.9

References

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

Transporters

Enzyme Details

1. 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

Takara K, Sakaeda T, Tanigawara Y, Nishiguchi K, Ohmoto N, Horinouchi M, Komada F, Ohnishi N, Yokoyama T, Okumura K: Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression. Eur J Pharm Sci. 2002 Aug;16(3):159-65. [PubMed:12128170 ]

Showing metabocard for Nisoldipine (HMDB0014545)

MOL for HMDB0014545 (Nisoldipine)

3D MOL for HMDB0014545 (Nisoldipine)

3D SDF for HMDB0014545 (Nisoldipine)

3D-SDF for HMDB0014545 (Nisoldipine)

PDB for HMDB0014545 (Nisoldipine)

3D PDB for HMDB0014545 (Nisoldipine)

SMILES for HMDB0014545 (Nisoldipine)

INCHI for HMDB0014545 (Nisoldipine)

Structure for HMDB0014545 (Nisoldipine)

3D Structure for HMDB0014545 (Nisoldipine)

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

References

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Transporters

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