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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014415

Secondary Accession Numbers

HMDB14415

Metabolite Identification

Common Name

Isradipine

Description

Isradipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. It is structurally related to felodipine, nifedipine, and nimodipine and is the most potent calcium-channel blocking agent of the DHP class. Isradipine binds to calcium channels with high affinity and specificity and inhibits calcium flux into cardiac and arterial smooth muscle cells. It exhibits greater selectivity towards arterial smooth muscle cells owing to alternative splicing of the alpha-1 subunit of the channel and increased prevalence of inactive channels in smooth muscle cells. Isradipine may be used to treat mild to moderate essential hypertension.

Structure

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

270
  Mrv0541 02231214332D          

 27 29  0  0  1  0            999 V2000
    3.0791    0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -1.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3660   -0.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.8294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -2.1572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 24  1  0  0  0  0
  2 19  1  0  0  0  0
  2 27  1  0  0  0  0
  3 16  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5 19  2  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  2  0  0  0  0
  8 21  2  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 16  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 15  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
 15 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

HMDB0249193
     RDKit          3D
BIDD:PXR0114
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8086    3.6239   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    2.4238   -1.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.9676   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870    2.6846   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.7018   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -0.0207   -2.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673    0.4110   -3.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.2668   -2.7470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -1.6972   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -3.0020   -2.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.9875   -1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.4948   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1982   -2.5541   -0.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.7497    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.1492    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -0.2068    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.4139    2.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.3171   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539    0.2737    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -0.7171    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.7246    2.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    0.2723    3.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    1.2639    2.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    2.3317    3.4444 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    2.9475    2.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    2.3327    1.3812 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1798    1.2481    1.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    3.5400   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    4.3955   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094    4.0249   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.3406   -3.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    0.4768   -2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.4326   -3.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -1.8426   -3.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -3.4410   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -3.7569   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4872   -2.8660   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -2.1298    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -0.3879    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.8564    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.4895    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -0.8573    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -1.1322    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -2.5022    2.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    1.1001   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.5219    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -1.4749    3.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    0.2850    4.6073 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
 15 17  1  0
 11 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 18  5  1  0
 27 19  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

270
  Mrv0541 02231214332D          

 27 29  0  0  1  0            999 V2000
    3.0791    0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -1.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3660   -0.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.8294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -2.1572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 24  1  0  0  0  0
  2 19  1  0  0  0  0
  2 27  1  0  0  0  0
  3 16  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5 19  2  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  2  0  0  0  0
  8 21  2  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 16  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 15  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
 15 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014415

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3

> <INCHI_KEY>
HMJIYCCIJYRONP-UHFFFAOYSA-N

> <FORMULA>
C19H21N3O5

> <MOLECULAR_WEIGHT>
371.3871

> <EXACT_MASS>
371.148120797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.38681687272389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
1.9989157586666682

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.329899293934086

> <JCHEM_POLAR_SURFACE_AREA>
103.55000000000001

> <JCHEM_REFRACTIVITY>
100.08420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isradipine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249193
     RDKit          3D
BIDD:PXR0114
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8086    3.6239   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    2.4238   -1.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.9676   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870    2.6846   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.7018   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -0.0207   -2.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673    0.4110   -3.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.2668   -2.7470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -1.6972   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -3.0020   -2.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.9875   -1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.4948   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1982   -2.5541   -0.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.7497    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.1492    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -0.2068    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.4139    2.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.3171   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539    0.2737    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -0.7171    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.7246    2.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    0.2723    3.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    1.2639    2.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    2.3317    3.4444 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    2.9475    2.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    2.3327    1.3812 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1798    1.2481    1.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    3.5400   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    4.3955   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094    4.0249   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.3406   -3.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    0.4768   -2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.4326   -3.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -1.8426   -3.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -3.4410   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -3.7569   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4872   -2.8660   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -2.1298    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -0.3879    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.8564    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.4895    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -0.8573    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -1.1322    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -2.5022    2.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    1.1001   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.5219    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -1.4749    3.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    0.2850    4.6073 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
 15 17  1  0
 11 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 18  5  1  0
 27 19  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 270                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   1.063   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.750   1.063   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -1.247   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.438  -2.787   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.750  -0.477   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.748   3.373   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      12.540  -1.548   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.540  -4.027   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.748   0.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   1.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   1.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   2.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   2.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -2.017   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -2.017   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   3.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416   0.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   3.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082  -3.557   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -3.557   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748  -4.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   0.293   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   1.063   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -1.247   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.083   0.293   0.000  0.00  0.00           C+0
CONECT    1   16   24                                                       
CONECT    2   19   27                                                       
CONECT    3   16                                                            
CONECT    4    7    8                                                       
CONECT    5   19                                                            
CONECT    6   13   14                                                       
CONECT    7    4   15                                                       
CONECT    8    4   21                                                       
CONECT    9   10   11   12                                                  
CONECT   10    9   13   16                                                  
CONECT   11    9   14   19                                                  
CONECT   12    9   15   17                                                  
CONECT   13    6   10   18                                                  
CONECT   14    6   11   20                                                  
CONECT   15    7   12   21                                                  
CONECT   16    1    3   10                                                  
CONECT   17   12   22                                                       
CONECT   18   13                                                            
CONECT   19    2    5   11                                                  
CONECT   20   14                                                            
CONECT   21    8   15   23                                                  
CONECT   22   17   23                                                       
CONECT   23   21   22                                                       
CONECT   24    1   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    2                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0014415
HETATM    1  C1  UNL     1      -3.610   2.870   2.415  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.589   2.272   1.659  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.559   2.331   0.275  1.00  0.00           C  
HETATM    4  O2  UNL     1      -3.491   2.945  -0.249  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.463   1.684  -0.427  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.477   1.770  -1.754  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.563   2.489  -2.420  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.443   1.171  -2.525  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.590   0.490  -1.866  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.689  -0.147  -2.685  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.645   0.380  -0.569  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.765  -0.355   0.092  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.796  -0.447   1.347  1.00  0.00           O  
HETATM   14  O4  UNL     1       2.781  -0.947  -0.596  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.854  -1.648  -0.033  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.188  -1.025  -0.321  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.905  -3.092  -0.475  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.386   0.965   0.300  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.040  -0.074   1.138  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.123   0.093   2.490  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.701  -0.879   3.320  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.188  -2.018   2.745  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.102  -2.186   1.382  1.00  0.00           C  
HETATM   24  N2  UNL     1      -2.491  -3.185   0.572  1.00  0.00           N  
HETATM   25  O5  UNL     1      -2.186  -2.870  -0.654  1.00  0.00           O  
HETATM   26  N3  UNL     1      -1.612  -1.705  -0.694  1.00  0.00           N  
HETATM   27  C19 UNL     1      -1.529  -1.217   0.573  1.00  0.00           C  
HETATM   28  H1  UNL     1      -4.455   3.226   1.773  1.00  0.00           H  
HETATM   29  H2  UNL     1      -3.166   3.786   2.889  1.00  0.00           H  
HETATM   30  H3  UNL     1      -3.963   2.241   3.253  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.568   2.030  -2.338  1.00  0.00           H  
HETATM   32  H5  UNL     1      -2.366   2.429  -3.540  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.524   3.572  -2.221  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.476   1.253  -3.592  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.447   0.112  -3.758  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.664   0.334  -2.512  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.661  -1.234  -2.596  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.711  -1.623   1.077  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.472  -0.343   0.493  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.080  -0.464  -1.287  1.00  0.00           H  
HETATM   41  H14 UNL     1       6.005  -1.793  -0.398  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.078  -3.695  -0.065  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.882  -3.150  -1.585  1.00  0.00           H  
HETATM   44  H17 UNL     1       4.897  -3.501  -0.151  1.00  0.00           H  
HETATM   45  H18 UNL     1       0.108   1.725   0.952  1.00  0.00           H  
HETATM   46  H19 UNL     1      -0.739   0.962   3.016  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.766  -0.743   4.388  1.00  0.00           H  
HETATM   48  H21 UNL     1      -2.643  -2.787   3.388  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   18
CONECT    6    7    8
CONECT    7   31   32   33
CONECT    8    9   34
CONECT    9   10   11   11
CONECT   10   35   36   37
CONECT   11   12   18
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   17   38
CONECT   16   39   40   41
CONECT   17   42   43   44
CONECT   18   19   45
CONECT   19   20   20   27
CONECT   20   21   46
CONECT   21   22   22   47
CONECT   22   23   48
CONECT   23   24   24   27
CONECT   24   25
CONECT   25   26
CONECT   26   27   27
END

HMDB0249193
     RDKit          3D
BIDD:PXR0114
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8086    3.6239   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    2.4238   -1.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.9676   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870    2.6846   -0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.7018   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -0.0207   -2.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673    0.4110   -3.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.2668   -2.7470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288   -1.6972   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -3.0020   -2.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.9875   -1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.4948   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1982   -2.5541   -0.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.7497    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.1492    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -0.2068    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -1.4139    2.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.3171   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539    0.2737    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -0.7171    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -0.7246    2.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    0.2723    3.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    1.2639    2.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461    2.3317    3.4444 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    2.9475    2.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664    2.3327    1.3812 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1798    1.2481    1.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    3.5400   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    4.3955   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094    4.0249   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.3406   -3.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    0.4768   -2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.4326   -3.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -1.8426   -3.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -3.4410   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -3.7569   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4872   -2.8660   -2.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -2.1298    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -0.3879    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.8564    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.4895    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -0.8573    2.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -1.1322    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -2.5022    2.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    1.1001   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.5219    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -1.4749    3.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    0.2850    4.6073 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
 15 17  1  0
 11 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 18  5  1  0
 27 19  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dynacirc	Kegg
(+/-)-isradipine	HMDB
Isradipin	HMDB
Isrodipine	HMDB
Isradipine, (+-)-isomer	MeSH, HMDB
Isradipine, (R)-isomer	MeSH, HMDB
Isradipine, (S)-isomer	MeSH, HMDB
Lomir	MeSH, HMDB

Chemical Formula

C₁₉H₂₁N₃O₅

Average Molecular Weight

371.3871

Monoisotopic Molecular Weight

371.148120797

IUPAC Name

3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Traditional Name

isradipine

CAS Registry Number

75695-93-1

SMILES

COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C

InChI Identifier

InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3

InChI Key

HMJIYCCIJYRONP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxadiazoles. These are organic compounds containing a benzene fused to an oxadiazole ring (a five-membered ring with two carbon atoms, one nitrogen atom, and one oxygen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxadiazoles

Sub Class

Not Available

Direct Parent

Benzoxadiazoles

Alternative Parents

Substituents

Benzoxadiazole
Dihydropyridinecarboxylic acid derivative
Dihydropyridine
Dicarboxylic acid or derivatives
Benzenoid
Hydropyridine
Azole
Heteroaromatic compound
Furazan
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Oxadiazole
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Azacycle
Enamine
Secondary aliphatic amine
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014415)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Isradipine Action Pathway (PathBank: SMP0000378)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.23 g/L	Not Available
LogP	2.901	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	3	ALOGPS
logP	2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	5.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.08 m³·mol⁻¹	ChemAxon
Polarizability	37.39 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.0	31661259
DarkChem	[M-H]-	182.203	31661259
DeepCCS	[M-2H]-	218.581	30932474
DeepCCS	[M+Na]+	194.175	30932474
AllCCS	[M+H]+	186.8	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.4	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	191.3	32859911
AllCCS	[M+Na-2H]-	191.4	32859911
AllCCS	[M+HCOO]-	191.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isradipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C	3651.6	Standard polar	33892256
Isradipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C	2778.2	Standard non polar	33892256
Isradipine	COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C	2787.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isradipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	2898.2	Semi standard non polar	33892256
Isradipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	2498.3	Standard non polar	33892256
Isradipine,1TMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	3977.0	Standard polar	33892256
Isradipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	3093.5	Semi standard non polar	33892256
Isradipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	2716.0	Standard non polar	33892256
Isradipine,1TBDMS,isomer #1	COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12	3969.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6059000000-e9ec514baf6b881462eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine LC-ESI-qTof , Positive-QTOF	splash10-0006-0009000000-3c8fe8c9d5e94c018299	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine LC-ESI-qTof , Positive-QTOF	splash10-03dl-2589000000-e01ef029445c948c93e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine , positive-QTOF	splash10-0006-0009000000-3c8fe8c9d5e94c018299	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine , positive-QTOF	splash10-03dl-2589000000-e01ef029445c948c93e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine 35V, Negative-QTOF	splash10-014i-1910000000-dfed2a9ad69e197388ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isradipine 35V, Positive-QTOF	splash10-08gl-0093000000-018aae73f171426e9786	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 10V, Positive-QTOF	splash10-0006-0019000000-14fbaf7e209b164eca31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 20V, Positive-QTOF	splash10-01wb-1094000000-f17e6d7b6c23adad32d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 40V, Positive-QTOF	splash10-001i-1192000000-f7640fb5efbe178b4418	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 10V, Negative-QTOF	splash10-00di-1029000000-a657ce350be64e5e10cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 20V, Negative-QTOF	splash10-05gi-3169000000-482100e723136208aa67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 40V, Negative-QTOF	splash10-0aor-6191000000-85fa9ee77cf0b2b9a9fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 10V, Negative-QTOF	splash10-00di-0109000000-16c47c66d4fad17b5454	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 20V, Negative-QTOF	splash10-05fr-2019000000-e3409ae5fd7b715f6360	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 40V, Negative-QTOF	splash10-014i-0393000000-894b314cbe04d7da3127	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 10V, Positive-QTOF	splash10-03k9-0009000000-91e2afb1e32f59d7a22e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 20V, Positive-QTOF	splash10-0h3r-0094000000-90ceb2e95c063a9a8953	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isradipine 40V, Positive-QTOF	splash10-0fka-1292000000-d08a6d4825f5eb1d6fab	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
Isradipine 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 DB00270	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00270	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00270

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isradipine

METLIN ID

Not Available

PubChem Compound

Not Available

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

Fletcher H, Roberts G, Mullings A, Forrester T: An open trial comparing isradipine with hydralazine and methyl dopa in the treatment of patients with severe pre-eclampsia. J Obstet Gynaecol. 1999 May;19(3):235-8. [PubMed:15512286 ]
Johnson BA, Roache JD, Ait-Daoud N, Wallace C, Wells L, Dawes M, Wang Y: Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects. Int J Neuropsychopharmacol. 2005 Jun;8(2):203-13. [PubMed:15850499 ]
Ganz M, Mokabberi R, Sica DA: Comparison of blood pressure control with amlodipine and controlled-release isradipine: an open-label, drug substitution study. J Clin Hypertens (Greenwich). 2005 Apr;7(4 Suppl 1):27-31. [PubMed:15858400 ]
Hattori T, Wang PL: Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts. Eur J Med Res. 2006 Mar 27;11(3):93-6. [PubMed:16751108 ]

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. 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

Koschak A, Reimer D, Huber I, Grabner M, Glossmann H, Engel J, Striessnig J: alpha 1D (Cav1.3) subunits can form l-type Ca2+ channels activating at negative voltages. J Biol Chem. 2001 Jun 22;276(25):22100-6. Epub 2001 Apr 2. [PubMed:11285265 ]
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

3. 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

Berjukow S, Marksteiner R, Gapp F, Sinnegger MJ, Hering S: Molecular mechanism of calcium channel block by isradipine. Role of a drug-induced inactivated channel conformation. J Biol Chem. 2000 Jul 21;275(29):22114-20. [PubMed:10766758 ]
Hitzl M, Striessnig J, Neuhuber B, Flucher BE: A mutation in the beta interaction domain of the Ca(2+) channel alpha(1C) subunit reduces the affinity of the (+)-[(3)H]isradipine binding site. FEBS Lett. 2002 Jul 31;524(1-3):188-92. [PubMed:12135765 ]
Zuhlke RD, Bouron A, Soldatov NM, Reuter H: Ca2+ channel sensitivity towards the blocker isradipine is affected by alternative splicing of the human alpha1C subunit gene. FEBS Lett. 1998 May 8;427(2):220-4. [PubMed:9607315 ]

Enzyme Details

4. 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

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Voltage-dependent calcium channel subunit alpha-2/delta-2

General function:: Involved in calcium channel activity
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-type calcium channel (CACNA1A), N-type (CACNA1B), L-type (CACNA1C OR CACNA1D) and possibly T-type (CACNA1G). Overexpression induces apoptosis
Gene Name:: CACNA2D2
Uniprot ID:: Q9NY47
Molecular weight:: 129875.2

References

Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361 ]

Enzyme Details

6. Voltage-dependent T-type calcium channel subunit alpha-1H

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-1H gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by nickel and mibefradil. A particularity of this type of channels is an opening at quite negative potentials, and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes
Gene Name:: CACNA1H
Uniprot ID:: O95180
Molecular weight:: 259160.2

References

Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361 ]

Enzyme Details

7. 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

8. 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 ]

Showing metabocard for Isradipine (HMDB0014415)

MOL for HMDB0014415 (Isradipine)

3D MOL for HMDB0014415 (Isradipine)

3D SDF for HMDB0014415 (Isradipine)

3D-SDF for HMDB0014415 (Isradipine)

PDB for HMDB0014415 (Isradipine)

3D PDB for HMDB0014415 (Isradipine)

SMILES for HMDB0014415 (Isradipine)

INCHI for HMDB0014415 (Isradipine)

Structure for HMDB0014415 (Isradipine)

3D Structure for HMDB0014415 (Isradipine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References