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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014487

Secondary Accession Numbers

HMDB14487

Metabolite Identification

Common Name

Diltiazem

Description

Diltiazem is only found in individuals that have used or taken this drug. It is a benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem]Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, diltiazem, like verapamil, inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.

Structure

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

343
  Mrv0541 02231214372D          

 29 31  0  0  1  0            999 V2000
    3.3901   -0.5861    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0483   -0.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727    3.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3749    0.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0603   -1.3904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183   -2.1178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045    0.0589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7295    0.0589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2439   -0.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7053   -1.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    0.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4733   -1.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -1.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0113    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    1.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6534    2.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863   -1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9954   -2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    2.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2681    1.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 14  1  0  0  0  0
  9  2  1  1  0  0  0
  2 27  1  0  0  0  0
  3 10  2  0  0  0  0
  4 26  1  0  0  0  0
  4 29  1  0  0  0  0
  5 27  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 15  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  1  0  0  0
  9 10  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 21  2  0  0  0  0
 22 26  2  0  0  0  0
 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014487
     RDKit          3D
Diltiazem
 55 57  0  0  0  0  0  0  0  0999 V2000
   -6.4793    2.6820   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812    2.9584   -0.2965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.9168    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    0.6492    0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795   -0.3742    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.1738    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -1.2870    0.9622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5937   -0.8474    2.4188 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -1.0666    2.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7070   -1.3998    3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -1.5850    3.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687   -1.4411    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -1.1098    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.9221    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -0.5829   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    0.0764   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    1.5877   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    2.0789   -1.7172 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264    3.5083   -1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274    1.5257   -1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8880   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -0.2674   -1.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -1.7837   -0.1924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5493   -2.2220   -1.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -3.5195   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552   -3.9396   -2.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9541   -4.3941   -1.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    1.0878    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    2.1276    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7552    1.9173   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    2.2711    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0692    3.6084   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.5097    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -1.3642    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.1661    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5083    4.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710   -1.8536    4.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5883    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -0.9953    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632   -0.0496   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.3726   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    1.9615    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    2.0063   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    4.0127   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403    3.9041   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    3.8048   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985    1.1536   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0911    0.6528   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    2.2357   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -2.7184    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -3.1411   -3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9806   -4.2215   -3.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -4.8021   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    1.2365    0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4203    3.1121   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 15 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  6 28  1  0
 28 29  2  0
 29  3  1  0
 23  7  1  0
 14  9  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  1
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 26 51  1  0
 26 52  1  0
 26 53  1  0
 28 54  1  0
 29 55  1  0
M  END

343
  Mrv0541 02231214372D          

 29 31  0  0  1  0            999 V2000
    3.3901   -0.5861    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0483   -0.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727    3.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3749    0.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0603   -1.3904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183   -2.1178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045    0.0589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7295    0.0589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2439   -0.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7053   -1.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    0.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4733   -1.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -1.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0113    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    1.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6534    2.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863   -1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9954   -2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307    2.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2681    1.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 14  1  0  0  0  0
  9  2  1  1  0  0  0
  2 27  1  0  0  0  0
  3 10  2  0  0  0  0
  4 26  1  0  0  0  0
  4 29  1  0  0  0  0
  5 27  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 15  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  1  0  0  0
  9 10  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 21  2  0  0  0  0
 22 26  2  0  0  0  0
 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014487

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1

> <INCHI_KEY>
HSUGRBWQSSZJOP-RTWAWAEBSA-N

> <FORMULA>
C22H26N2O4S

> <MOLECULAR_WEIGHT>
414.518

> <EXACT_MASS>
414.16132802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.64570149671696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.7272518843333335

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.860751889993132

> <JCHEM_PKA_STRONGEST_BASIC>
8.175280193715892

> <JCHEM_POLAR_SURFACE_AREA>
59.080000000000005

> <JCHEM_REFRACTIVITY>
114.36630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diltiazem

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014487
     RDKit          3D
Diltiazem
 55 57  0  0  0  0  0  0  0  0999 V2000
   -6.4793    2.6820   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812    2.9584   -0.2965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.9168    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    0.6492    0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795   -0.3742    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.1738    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -1.2870    0.9622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5937   -0.8474    2.4188 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -1.0666    2.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7070   -1.3998    3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -1.5850    3.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687   -1.4411    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -1.1098    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.9221    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -0.5829   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    0.0764   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    1.5877   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    2.0789   -1.7172 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264    3.5083   -1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274    1.5257   -1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8880   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -0.2674   -1.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -1.7837   -0.1924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5493   -2.2220   -1.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -3.5195   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552   -3.9396   -2.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9541   -4.3941   -1.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    1.0878    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    2.1276    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7552    1.9173   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    2.2711    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0692    3.6084   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.5097    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -1.3642    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.1661    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5083    4.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710   -1.8536    4.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5883    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -0.9953    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632   -0.0496   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.3726   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    1.9615    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    2.0063   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    4.0127   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403    3.9041   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    3.8048   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985    1.1536   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0911    0.6528   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    2.2357   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -2.7184    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -3.1411   -3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9806   -4.2215   -3.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -4.8021   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    1.2365    0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4203    3.1121   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 15 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  6 28  1  0
 28 29  2  0
 29  3  1  0
 23  7  1  0
 14  9  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  1
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 26 51  1  0
 26 52  1  0
 26 53  1  0
 28 54  1  0
 29 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 343                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.328  -1.094   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.497   1.497   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.290  -0.751   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.616   5.660   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.900   0.340   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.446  -2.595   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.287  -3.953   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.288   0.110   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.828   0.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.789  -1.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.650  -3.556   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.058  -3.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.620   1.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.671  -2.595   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.083  -2.993   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.203  -4.861   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.332  -3.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.085   1.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.488   2.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.885  -5.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.439  -5.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.416   3.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.820   4.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.721  -3.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.058  -5.476   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.284   4.272   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.032   1.613   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.700   3.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080   5.775   0.000  0.00  0.00           C+0
CONECT    1    8   14                                                       
CONECT    2    9   27                                                       
CONECT    3   10                                                            
CONECT    4   26   29                                                       
CONECT    5   27                                                            
CONECT    6   10   11   12                                                  
CONECT    7   15   24   25                                                  
CONECT    8    1    9   13                                                  
CONECT    9    2    8   10                                                  
CONECT   10    3    6    9                                                  
CONECT   11    6   15                                                       
CONECT   12    6   14   16                                                  
CONECT   13    8   18   19                                                  
CONECT   14    1   12   17                                                  
CONECT   15    7   11                                                       
CONECT   16   12   20                                                       
CONECT   17   14   21                                                       
CONECT   18   13   22                                                       
CONECT   19   13   23                                                       
CONECT   20   16   21                                                       
CONECT   21   17   20                                                       
CONECT   22   18   26                                                       
CONECT   23   19   26                                                       
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    4   22   23                                                  
CONECT   27    2    5   28                                                  
CONECT   28   27                                                            
CONECT   29    4                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0014487
HETATM    1  C1  UNL     1      -6.479   2.682  -0.282  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.081   2.958  -0.296  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.210   1.917   0.011  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.656   0.649   0.324  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.780  -0.374   0.627  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.419  -0.174   0.631  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.506  -1.287   0.962  1.00  0.00           C  
HETATM    8  S1  UNL     1      -0.594  -0.847   2.419  1.00  0.00           S  
HETATM    9  C7  UNL     1       1.158  -1.067   2.356  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.707  -1.400   3.575  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.052  -1.585   3.699  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.869  -1.441   2.611  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.356  -1.110   1.380  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.981  -0.922   1.259  1.00  0.00           C  
HETATM   15  N1  UNL     1       1.666  -0.583  -0.110  1.00  0.00           N  
HETATM   16  C13 UNL     1       2.623   0.076  -0.923  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.595   1.588  -0.820  1.00  0.00           C  
HETATM   18  N2  UNL     1       3.638   2.079  -1.717  1.00  0.00           N  
HETATM   19  C15 UNL     1       3.726   3.508  -1.721  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.927   1.526  -1.403  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.361  -0.888  -0.657  1.00  0.00           C  
HETATM   22  O2  UNL     1       0.118  -0.267  -1.721  1.00  0.00           O  
HETATM   23  C18 UNL     1      -0.712  -1.784  -0.192  1.00  0.00           C  
HETATM   24  O3  UNL     1      -1.549  -2.222  -1.234  1.00  0.00           O  
HETATM   25  C19 UNL     1      -1.654  -3.520  -1.667  1.00  0.00           C  
HETATM   26  C20 UNL     1      -2.555  -3.940  -2.776  1.00  0.00           C  
HETATM   27  O4  UNL     1      -0.954  -4.394  -1.097  1.00  0.00           O  
HETATM   28  C21 UNL     1      -1.962   1.088   0.320  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.847   2.128   0.012  1.00  0.00           C  
HETATM   30  H1  UNL     1      -6.755   1.917  -1.031  1.00  0.00           H  
HETATM   31  H2  UNL     1      -6.729   2.271   0.731  1.00  0.00           H  
HETATM   32  H3  UNL     1      -7.069   3.608  -0.382  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.735   0.510   0.317  1.00  0.00           H  
HETATM   34  H5  UNL     1      -4.195  -1.364   0.869  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.164  -2.166   1.254  1.00  0.00           H  
HETATM   36  H7  UNL     1       1.026  -1.508   4.429  1.00  0.00           H  
HETATM   37  H8  UNL     1       3.471  -1.854   4.694  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.950  -1.588   2.705  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.974  -0.995   0.536  1.00  0.00           H  
HETATM   40  H11 UNL     1       2.163  -0.050  -1.990  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.588  -0.373  -1.120  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.695   1.961   0.199  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.641   2.006  -1.210  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.987   4.013  -2.349  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.640   3.904  -0.673  1.00  0.00           H  
HETATM   46  H17 UNL     1       4.764   3.805  -2.041  1.00  0.00           H  
HETATM   47  H18 UNL     1       4.999   1.154  -0.377  1.00  0.00           H  
HETATM   48  H19 UNL     1       5.091   0.653  -2.098  1.00  0.00           H  
HETATM   49  H20 UNL     1       5.756   2.236  -1.649  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.184  -2.718   0.170  1.00  0.00           H  
HETATM   51  H22 UNL     1      -3.262  -3.141  -3.044  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.981  -4.222  -3.690  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.166  -4.802  -2.430  1.00  0.00           H  
HETATM   54  H25 UNL     1      -0.907   1.237   0.326  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.420   3.112  -0.228  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4   29
CONECT    4    5   33
CONECT    5    6    6   34
CONECT    6    7   28
CONECT    7    8   23   35
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   36
CONECT   11   12   12   37
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15
CONECT   15   16   21
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   19   20
CONECT   19   44   45   46
CONECT   20   47   48   49
CONECT   21   22   22   23
CONECT   23   24   50
CONECT   24   25
CONECT   25   26   27   27
CONECT   26   51   52   53
CONECT   28   29   29   54
CONECT   29   55
END

HMDB0014487
     RDKit          3D
Diltiazem
 55 57  0  0  0  0  0  0  0  0999 V2000
   -6.4793    2.6820   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812    2.9584   -0.2965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101    1.9168    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    0.6492    0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795   -0.3742    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.1738    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -1.2870    0.9622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5937   -0.8474    2.4188 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -1.0666    2.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7070   -1.3998    3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -1.5850    3.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687   -1.4411    2.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -1.1098    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.9221    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -0.5829   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    0.0764   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    1.5877   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384    2.0789   -1.7172 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264    3.5083   -1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274    1.5257   -1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8880   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -0.2674   -1.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -1.7837   -0.1924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5493   -2.2220   -1.2340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540   -3.5195   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5552   -3.9396   -2.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9541   -4.3941   -1.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    1.0878    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469    2.1276    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7552    1.9173   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289    2.2711    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0692    3.6084   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7353    0.5097    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1946   -1.3642    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -2.1661    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5083    4.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710   -1.8536    4.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5883    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -0.9953    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632   -0.0496   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.3726   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    1.9615    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    2.0063   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    4.0127   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403    3.9041   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    3.8048   -2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985    1.1536   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0911    0.6528   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    2.2357   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -2.7184    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619   -3.1411   -3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9806   -4.2215   -3.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -4.8021   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    1.2365    0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4203    3.1121   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 15 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  6 28  1  0
 28 29  2  0
 29  3  1  0
 23  7  1  0
 14  9  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  1
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 26 51  1  0
 26 52  1  0
 26 53  1  0
 28 54  1  0
 29 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-cis-5-[2-(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate ester	ChEBI
(2S,3S)-5-(2-(Dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate	ChEBI
(2S-cis)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one	ChEBI
Acetic acid (2S,3S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester	ChEBI
D-cis-Diltiazem	ChEBI
Diltiazemum	ChEBI
Surazem	Kegg
(+)-cis-5-[2-(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetic acid ester	Generator
(2S,3S)-5-(2-(Dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetic acid	Generator
Acetate (2S,3S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester	Generator
Cardil	HMDB
Aldizem	HMDB
Dilren	HMDB
Watson pharmaceuticals brand OF diltazem	HMDB
CRD 401	HMDB
CRD-401	HMDB
Cardizem	HMDB
Dilacor	HMDB
Dilacor XR	HMDB
Diltiazem hydrochloride	HMDB
Dilzem	HMDB
Tiazac	HMDB
Biovail brand OF diltiazem hydrochloride	HMDB
Diltiazem malate	HMDB

Chemical Formula

C₂₂H₂₆N₂O₄S

Average Molecular Weight

414.518

Monoisotopic Molecular Weight

414.16132802

IUPAC Name

(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate

Traditional Name

diltiazem

CAS Registry Number

42399-41-7

SMILES

COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1

InChI Key

HSUGRBWQSSZJOP-RTWAWAEBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazepines. These are organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazepines

Sub Class

Not Available

Direct Parent

Benzothiazepines

Alternative Parents

Substituents

Benzothiazepine
Phenoxy compound
Aryl thioether
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Alkylarylthioether
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Thioether
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate (CHEBI:101278 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (PMID: 25037050)

Cellular substructure

Membrane (HMDB: HMDB0014487)

Source

Exogenous

Exogenous (HMDB: HMDB0014487)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Diltiazem Action Pathway (PathBank: SMP0000359)

Role

Biological role

Calcium antagonist (HMDB: HMDB0014487)

Industrial application

Antihypertensive agent (HMDB: HMDB0014487)
Vasodilator agent (HMDB: HMDB0014487)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.017 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	197.8	30932474
[M+H]+	Not Available	196.111	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001102

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.09	ALOGPS
logP	2.73	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	8.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.37 m³·mol⁻¹	ChemAxon
Polarizability	43.65 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]+	199.854	31661259
DarkChem	[M-H]-	200.221	31661259
DeepCCS	[M+H]+	195.831	30932474
DeepCCS	[M-H]-	193.473	30932474
DeepCCS	[M-2H]-	227.067	30932474
DeepCCS	[M+Na]+	202.179	30932474
AllCCS	[M+H]+	199.7	32859911
AllCCS	[M+H-H2O]+	197.3	32859911
AllCCS	[M+NH4]+	201.9	32859911
AllCCS	[M+Na]+	202.5	32859911
AllCCS	[M-H]-	199.1	32859911
AllCCS	[M+Na-2H]-	199.5	32859911
AllCCS	[M+HCOO]-	200.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diltiazem	COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O	4619.2	Standard polar	33892256
Diltiazem	COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O	3055.0	Standard non polar	33892256
Diltiazem	COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O	3056.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diltiazem GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-9646000000-04d2eb286617fa811190	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diltiazem GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ab9-9200000000-b1095b8fe5973d23fdd6	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diltiazem 40V, Positive-QTOF	splash10-0fb9-0900000000-96509d36ba030e8f98c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diltiazem 10V, Positive-QTOF	splash10-014i-0201900000-26955403b59e6618fe76	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diltiazem 20V, Positive-QTOF	splash10-004i-0901100000-71e8128140c5e1ca0c52	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 10V, Positive-QTOF	splash10-00xr-3109700000-d386c5de1a87c11cbc6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 20V, Positive-QTOF	splash10-00di-7973000000-0bc5fc09ba611f5ad1fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 40V, Positive-QTOF	splash10-05fr-8911000000-3f9afe9e89e028c0d258	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 10V, Negative-QTOF	splash10-0a4i-9003300000-aa0d02f7d6ac5f92863e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 20V, Negative-QTOF	splash10-0a4i-9138100000-f2b6df8ef6a8cb7aed70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 40V, Negative-QTOF	splash10-0pb9-7951000000-c5814417a1eb6c5de03b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 10V, Positive-QTOF	splash10-014i-0001900000-8a381f5579f5f7ad42f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 20V, Positive-QTOF	splash10-00di-6918100000-310ffaa05668b4014162	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 40V, Positive-QTOF	splash10-0229-6958000000-c55c00ddc94a8d826551	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 10V, Negative-QTOF	splash10-03di-1023900000-78474bb391c4e477c10b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 20V, Negative-QTOF	splash10-0a4i-9188100000-db8c547169ab233cd8d1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diltiazem 40V, Negative-QTOF	splash10-0nov-3149000000-652c4505661022e2d0b6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Diltiazem 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 DB00343	21059682	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00343	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB00343

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35850

KEGG Compound ID

C06958

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diltiazem

METLIN ID

Not Available

PubChem Compound

39186

PDB ID

Not Available

ChEBI ID

101278

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 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 ]
Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 ]

Enzyme Details

2. Cytochrome P450 2C9

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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

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

References

Kosuge K, Jun Y, Watanabe H, Kimura M, Nishimoto M, Ishizaki T, Ohashi K: Effects of CYP3A4 inhibition by diltiazem on pharmacokinetics and dynamics of diazepam in relation to CYP2C19 genotype status. Drug Metab Dispos. 2001 Oct;29(10):1284-9. [PubMed:11560871 ]
McGinnity DF, Parker AJ, Soars M, Riley RJ: Automated definition of the enzymology of drug oxidation by the major human drug metabolizing cytochrome P450s. Drug Metab Dispos. 2000 Nov;28(11):1327-34. [PubMed:11038161 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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. 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

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

6. 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

7. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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

8. Voltage-dependent calcium channel gamma-1 subunit

General function:: Involved in voltage-gated calcium channel activity
Specific function:: This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only as a multiple subunit complex
Gene Name:: CACNG1
Uniprot ID:: Q06432
Molecular weight:: 25028.1

References

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 ]
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 ]
Budriesi R, Ioan P, Carosati E, Cruciani G, Zhorov BS, Chiarini A: Ligands of diltiazem binding site: an overview of some chemotypes. Mini Rev Med Chem. 2009 Oct;9(12):1379-88. [PubMed:19929811 ]
Romero M, Sanchez I, Pujol MD: New advances in the field of calcium channel antagonists: cardiovascular effects and structure-activity relationships. Curr Med Chem Cardiovasc Hematol Agents. 2003 Jun;1(2):113-41. [PubMed:15320693 ]

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

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
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 ]
Saeki T, Ueda K, Tanigawara Y, Hori R, Komano T: P-glycoprotein-mediated transcellular transport of MDR-reversing agents. FEBS Lett. 1993 Jun 7;324(1):99-102. [PubMed:8099333 ]

Showing metabocard for Diltiazem (HMDB0014487)

MOL for HMDB0014487 (Diltiazem)

3D MOL for HMDB0014487 (Diltiazem)

3D SDF for HMDB0014487 (Diltiazem)

3D-SDF for HMDB0014487 (Diltiazem)

PDB for HMDB0014487 (Diltiazem)

3D PDB for HMDB0014487 (Diltiazem)

SMILES for HMDB0014487 (Diltiazem)

INCHI for HMDB0014487 (Diltiazem)

Structure for HMDB0014487 (Diltiazem)

3D Structure for HMDB0014487 (Diltiazem)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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