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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (17)transporters (1) Show 18 proteins XML

enzymes (17)transporters (1) Show 18 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-02-16 09:20:18 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001850

Secondary Accession Numbers

HMDB0014799
HMDB01850
HMDB14799

Metabolite Identification

Common Name

Verapamil

Description

Verapamil is only found in individuals that have used or taken this drug. Verapamil is a calcium channel blocker that is a class IV anti-arrhythmia agent. [PubChem]Verapamil inhibits voltage-dependent calcium channels. Specifically, its effect on L-type calcium channels in the heart causes a reduction in ionotropy and chronotropy, thuis reducing heart rate and blood pressure. Verapamil's mechanism of effect in cluster headache is thought to be linked to its calcium-channel blocker effect, but which channel subtypes are involved is presently not known. [PubChem] Calcium channel antagonists can be quite toxic. In the management of poisoning, early recognition is critical. Calcium channel antagonists are frequently prescribed, and the potential for serious morbidity and mortality with over dosage is significant. Ingestion of these agents should be suspected in any patient who presents in an overdose situation with unexplained hypotension and conduction abnormalities. The potential for toxicity should be noted in patients with underlying hepatic or renal dysfunction who are receiving therapeutic doses. (PMID 8213877 ).

Structure

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

661
  Mrv1652305271900322D          

 33 34  0  0  1  0            999 V2000
    2.3645   -2.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2686    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0936    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5061    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2187    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 28  1  0  0  0  0
  2 23  1  0  0  0  0
  2 31  1  0  0  0  0
  3 27  1  0  0  0  0
  3 32  1  0  0  0  0
  4 30  1  0  0  0  0
  4 33  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  3  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0251100
     RDKit          3D
Dexverapamil
 71 72  0  0  0  0  0  0  0  0999 V2000
    6.5350    4.3703    2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    2.9697    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    2.3491    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801    3.0787    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.4282   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.0661   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.4356   -1.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -0.0261   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9216   -0.6431   -1.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.0850   -2.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.9815   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.1142   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -1.3127   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.2820    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.7152    1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -3.8166    1.1838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5049   -0.5952    0.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196    0.3671    1.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2953    1.0059    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9005    0.6925   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0646    1.2745   -0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7102    2.2488   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3220   -0.2675   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059   -0.6052   -2.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3223   -1.5756   -3.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1508   -0.8851   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.7898    2.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6366   -1.5940    2.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    0.6476    2.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3938   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    1.0024    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    0.2652    1.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0506   -1.1087    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    4.5292    2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537    4.7431    2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047    4.8868    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004    4.1240    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530    3.0107   -1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -0.4279   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.1422   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434   -0.7132   -0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8469   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571    1.1527   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.2084   -3.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.2847   -2.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018   -2.3713   -2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -2.6434   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -1.7723    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -3.1648   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.2583   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174   -1.7533   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    0.6637    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7579    1.7636    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9977    3.0672    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1525    1.8134    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    2.7104   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9740   -2.4828   -2.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091   -1.9325   -3.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.1289   -3.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7192   -1.6223   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.8121    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.0494    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.7135    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -2.6114    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327    0.6928    2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    1.2198    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447    1.1450    3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897   -0.6770   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9141   -1.4710    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1082   -1.6560    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3001   -1.3218   -0.0371 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  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 26 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 18 52  1  0
 19 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END

661
  Mrv1652305271900322D          

 33 34  0  0  1  0            999 V2000
    2.3645   -2.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2686    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0936    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5061    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2187    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 28  1  0  0  0  0
  2 23  1  0  0  0  0
  2 31  1  0  0  0  0
  3 27  1  0  0  0  0
  3 32  1  0  0  0  0
  4 30  1  0  0  0  0
  4 33  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  3  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001850

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3

> <INCHI_KEY>
SGTNSNPWRIOYBX-UHFFFAOYSA-N

> <FORMULA>
C27H38N2O4

> <MOLECULAR_WEIGHT>
454.6016

> <EXACT_MASS>
454.283157714

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.69513416927456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

> <ALOGPS_LOGP>
5.23

> <JCHEM_LOGP>
5.043185821000002

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.67844357225492

> <JCHEM_POLAR_SURFACE_AREA>
63.95

> <JCHEM_REFRACTIVITY>
132.6479

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
veraβ

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251100
     RDKit          3D
Dexverapamil
 71 72  0  0  0  0  0  0  0  0999 V2000
    6.5350    4.3703    2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    2.9697    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    2.3491    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801    3.0787    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.4282   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.0661   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.4356   -1.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -0.0261   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9216   -0.6431   -1.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.0850   -2.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.9815   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.1142   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -1.3127   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.2820    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.7152    1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -3.8166    1.1838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5049   -0.5952    0.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196    0.3671    1.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2953    1.0059    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9005    0.6925   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0646    1.2745   -0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7102    2.2488   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3220   -0.2675   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059   -0.6052   -2.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3223   -1.5756   -3.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1508   -0.8851   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.7898    2.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6366   -1.5940    2.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    0.6476    2.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3938   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    1.0024    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    0.2652    1.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0506   -1.1087    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    4.5292    2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537    4.7431    2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047    4.8868    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004    4.1240    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530    3.0107   -1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -0.4279   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.1422   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434   -0.7132   -0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8469   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571    1.1527   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.2084   -3.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.2847   -2.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018   -2.3713   -2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -2.6434   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -1.7723    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -3.1648   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.2583   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174   -1.7533   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    0.6637    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7579    1.7636    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9977    3.0672    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1525    1.8134    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    2.7104   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9740   -2.4828   -2.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091   -1.9325   -3.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.1289   -3.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7192   -1.6223   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.8121    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.0494    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.7135    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -2.6114    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327    0.6928    2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    1.2198    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447    1.1450    3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897   -0.6770   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9141   -1.4710    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1082   -1.6560    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3001   -1.3218   -0.0371 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  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 26 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 18 52  1  0
 19 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 661                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.414  -3.823   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081  -5.363   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.632   2.131   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.172   4.799   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.701   3.465   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.001   0.798   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   0.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   2.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621   0.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.391   2.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.742   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.931   2.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   3.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   3.108   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.541   0.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -1.513   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -1.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.241   3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -3.053   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.931   4.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -3.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.011   4.799   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -3.823   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.551   4.799   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.321   3.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.321   6.133   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.861   3.465   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080  -3.053   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.861   6.133   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.632   4.799   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415  -6.133   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.172   2.131   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.942   6.133   0.000  0.00  0.00           C+0
CONECT    1   19   28                                                       
CONECT    2   23   31                                                       
CONECT    3   27   32                                                       
CONECT    4   30   33                                                       
CONECT    5   12   18   20                                                  
CONECT    6   15                                                            
CONECT    7    8    9   11   15                                             
CONECT    8    7   13   14                                                  
CONECT    9    7   10                                                       
CONECT   10    9   12                                                       
CONECT   11    7   16   17                                                  
CONECT   12    5   10                                                       
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    6    7                                                       
CONECT   16   11   19                                                       
CONECT   17   11   21                                                       
CONECT   18    5   22                                                       
CONECT   19    1   16   23                                                  
CONECT   20    5                                                            
CONECT   21   17   23                                                       
CONECT   22   18   24                                                       
CONECT   23    2   19   21                                                  
CONECT   24   22   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24   29                                                       
CONECT   27    3   25   30                                                  
CONECT   28    1                                                            
CONECT   29   26   30                                                       
CONECT   30    4   27   29                                                  
CONECT   31    2                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0251100
HETATM    1  C1  UNL     1       6.535   4.370   2.054  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.656   2.970   1.789  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.780   2.349   0.917  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.780   3.079   0.299  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.933   2.428  -0.560  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.050   1.066  -0.827  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.116   0.436  -1.786  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.892  -0.026  -1.011  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.922  -0.643  -1.809  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.199   0.085  -2.758  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.661  -1.981  -1.550  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.039  -2.114  -0.171  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.282  -1.313  -0.302  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.237  -1.282   0.829  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.675  -2.715   1.026  1.00  0.00           C  
HETATM   16  N2  UNL     1      -2.988  -3.817   1.184  1.00  0.00           N  
HETATM   17  C14 UNL     1      -3.505  -0.595   0.430  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.120   0.367   1.214  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.295   1.006   0.843  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.901   0.693  -0.347  1.00  0.00           C  
HETATM   21  O2  UNL     1      -7.065   1.275  -0.795  1.00  0.00           O  
HETATM   22  C18 UNL     1      -7.710   2.249  -0.012  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.322  -0.268  -1.169  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.906  -0.605  -2.370  1.00  0.00           O  
HETATM   25  C20 UNL     1      -5.322  -1.576  -3.198  1.00  0.00           C  
HETATM   26  C21 UNL     1      -4.151  -0.885  -0.770  1.00  0.00           C  
HETATM   27  C22 UNL     1      -1.736  -0.790   2.143  1.00  0.00           C  
HETATM   28  C23 UNL     1      -0.637  -1.594   2.768  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.246   0.648   2.072  1.00  0.00           C  
HETATM   30  C25 UNL     1       5.057   0.394  -0.186  1.00  0.00           C  
HETATM   31  C26 UNL     1       5.928   1.002   0.681  1.00  0.00           C  
HETATM   32  O4  UNL     1       6.926   0.265   1.296  1.00  0.00           O  
HETATM   33  C27 UNL     1       7.051  -1.109   1.028  1.00  0.00           C  
HETATM   34  H1  UNL     1       5.513   4.529   2.464  1.00  0.00           H  
HETATM   35  H2  UNL     1       7.354   4.743   2.680  1.00  0.00           H  
HETATM   36  H3  UNL     1       6.605   4.887   1.077  1.00  0.00           H  
HETATM   37  H4  UNL     1       4.700   4.124   0.515  1.00  0.00           H  
HETATM   38  H5  UNL     1       3.153   3.011  -1.038  1.00  0.00           H  
HETATM   39  H6  UNL     1       3.641  -0.428  -2.249  1.00  0.00           H  
HETATM   40  H7  UNL     1       2.897   1.142  -2.589  1.00  0.00           H  
HETATM   41  H8  UNL     1       2.243  -0.713  -0.222  1.00  0.00           H  
HETATM   42  H9  UNL     1       1.446   0.847  -0.483  1.00  0.00           H  
HETATM   43  H10 UNL     1       0.057   1.153  -2.406  1.00  0.00           H  
HETATM   44  H11 UNL     1       0.810   0.208  -3.687  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.813  -0.285  -2.988  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.102  -2.371  -2.289  1.00  0.00           H  
HETATM   47  H14 UNL     1       1.554  -2.643  -1.551  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.678  -1.772   0.607  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.256  -3.165  -0.021  1.00  0.00           H  
HETATM   50  H17 UNL     1      -1.091  -0.258  -0.625  1.00  0.00           H  
HETATM   51  H18 UNL     1      -1.817  -1.753  -1.200  1.00  0.00           H  
HETATM   52  H19 UNL     1      -3.717   0.664   2.156  1.00  0.00           H  
HETATM   53  H20 UNL     1      -5.758   1.764   1.484  1.00  0.00           H  
HETATM   54  H21 UNL     1      -6.998   3.067   0.203  1.00  0.00           H  
HETATM   55  H22 UNL     1      -8.153   1.813   0.924  1.00  0.00           H  
HETATM   56  H23 UNL     1      -8.572   2.710  -0.557  1.00  0.00           H  
HETATM   57  H24 UNL     1      -4.974  -2.483  -2.673  1.00  0.00           H  
HETATM   58  H25 UNL     1      -6.109  -1.932  -3.915  1.00  0.00           H  
HETATM   59  H26 UNL     1      -4.511  -1.129  -3.843  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.719  -1.622  -1.400  1.00  0.00           H  
HETATM   61  H28 UNL     1      -2.589  -0.812   2.849  1.00  0.00           H  
HETATM   62  H29 UNL     1       0.333  -1.049   2.770  1.00  0.00           H  
HETATM   63  H30 UNL     1      -0.841  -1.714   3.891  1.00  0.00           H  
HETATM   64  H31 UNL     1      -0.519  -2.611   2.409  1.00  0.00           H  
HETATM   65  H32 UNL     1      -0.133   0.693   2.059  1.00  0.00           H  
HETATM   66  H33 UNL     1      -1.629   1.220   1.225  1.00  0.00           H  
HETATM   67  H34 UNL     1      -1.545   1.145   3.010  1.00  0.00           H  
HETATM   68  H35 UNL     1       5.190  -0.677  -0.362  1.00  0.00           H  
HETATM   69  H36 UNL     1       7.914  -1.471   1.621  1.00  0.00           H  
HETATM   70  H37 UNL     1       6.108  -1.656   1.245  1.00  0.00           H  
HETATM   71  H38 UNL     1       7.300  -1.322  -0.037  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3
CONECT    3    4    4   31
CONECT    4    5   37
CONECT    5    6    6   38
CONECT    6    7   30
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   11
CONECT   10   43   44   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   17   27
CONECT   15   16   16   16
CONECT   17   18   18   26
CONECT   18   19   52
CONECT   19   20   20   53
CONECT   20   21   23
CONECT   21   22
CONECT   22   54   55   56
CONECT   23   24   26   26
CONECT   24   25
CONECT   25   57   58   59
CONECT   26   60
CONECT   27   28   29   61
CONECT   28   62   63   64
CONECT   29   65   66   67
CONECT   30   31   31   68
CONECT   31   32
CONECT   32   33
CONECT   33   69   70   71
END

HMDB0251100
     RDKit          3D
Dexverapamil
 71 72  0  0  0  0  0  0  0  0999 V2000
    6.5350    4.3703    2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    2.9697    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    2.3491    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801    3.0787    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.4282   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.0661   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.4356   -1.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -0.0261   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9216   -0.6431   -1.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.0850   -2.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.9815   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.1142   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -1.3127   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.2820    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -2.7152    1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -3.8166    1.1838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5049   -0.5952    0.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196    0.3671    1.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2953    1.0059    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9005    0.6925   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0646    1.2745   -0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7102    2.2488   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3220   -0.2675   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059   -0.6052   -2.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3223   -1.5756   -3.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1508   -0.8851   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.7898    2.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6366   -1.5940    2.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    0.6476    2.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3938   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    1.0024    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    0.2652    1.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0506   -1.1087    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    4.5292    2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537    4.7431    2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047    4.8868    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004    4.1240    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530    3.0107   -1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407   -0.4279   -2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.1422   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434   -0.7132   -0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8469   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571    1.1527   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.2084   -3.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.2847   -2.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018   -2.3713   -2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -2.6434   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -1.7723    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558   -3.1648   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.2583   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174   -1.7533   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    0.6637    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7579    1.7636    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9977    3.0672    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1525    1.8134    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    2.7104   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9740   -2.4828   -2.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091   -1.9325   -3.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.1289   -3.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7192   -1.6223   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.8121    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.0494    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.7135    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -2.6114    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327    0.6928    2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    1.2198    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5447    1.1450    3.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897   -0.6770   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9141   -1.4710    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1082   -1.6560    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3001   -1.3218   -0.0371 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  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 26 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 18 52  1  0
 19 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CP-165331Verapamil	HMDB
Covera-HS	HMDB
Verelan	HMDB
Isoptin	HMDB
D-365Iproveratril	HMDB
CP-16533-1Calan	HMDB
Tarka	HMDB
Akilen	HMDB
Anpec	HMDB
Apo-verap	HMDB
Arpamyl LP	HMDB
Berkatens	HMDB
Calan	HMDB
Calan SR	HMDB
Calaptin	HMDB
Calaptin 240 SR	HMDB
Calcan	HMDB
Cardiabeltin	HMDB
Cardiagutt	HMDB
Cardibeltin	HMDB
Cardioprotect	HMDB
Caveril	HMDB
Civicor	HMDB
Civicor retard	HMDB
Coraver	HMDB
Cordilox	HMDB
Cordilox SR	HMDB
Corpamil	HMDB
D-365	HMDB
delta-365	HMDB
Dignover	HMDB
Dilacoran	HMDB
Dilacoran hta	HMDB
Durasoptin	HMDB
Elthon	HMDB
Falicard	HMDB
Finoptin	HMDB
Flamon	HMDB
Geangin	HMDB
Harteze	HMDB
Hexasoptin	HMDB
Hexasoptin retard	HMDB
Hormitol	HMDB
Ikacor	HMDB
Ikapress	HMDB
Inselon	HMDB
Iproveratril	HMDB
Isoptin retard	HMDB
Isoptin SR	HMDB
Isoptine	HMDB
Isoptino	HMDB
Isotopin	HMDB
Izoptin	HMDB
Jenapamil	HMDB
Lekoptin	HMDB
Lodixal	HMDB
Magotiron	HMDB
Manidon	HMDB
Manidon retard	HMDB
Novapamyl LP	HMDB
Novo-veramil	HMDB
Nu-verap	HMDB
Ormil	HMDB
Praecicor	HMDB
Quasar	HMDB
Rapam	HMDB
Robatelan	HMDB
Securon	HMDB
Univer	HMDB
Univex	HMDB
Vasolan	HMDB
Vasomil	HMDB
Vasopten	HMDB
Vera-sanorania	HMDB
Verabeta	HMDB
Veracaps SR	HMDB
Veracor	HMDB
Verahexal	HMDB
Veraloc	HMDB
Veramex	HMDB
Veramil	HMDB
Verapamil acis	HMDB
Verapamil al	HMDB
Verapamil atid	HMDB
Verapamil basics	HMDB
Verapamil ebewe	HMDB
Verapamil HCL	HMDB
Verapamil henning	HMDB
Verapamil injection	HMDB
Verapamil MSD	HMDB
Verapamil NM	HMDB
Verapamil NM pharma	HMDB
Verapamil nordic	HMDB
Verapamil PB	HMDB
Verapamil riker	HMDB
Verapamil SR	HMDB
Verapamil verla	HMDB
Verapamil-abz	HMDB
Verapamilo	HMDB
Verapamilum	HMDB
Verapin	HMDB
Verapress 240 SR	HMDB
Verasal	HMDB
Verasifar	HMDB
Veratensin	HMDB
Verdilac	HMDB
Verelan PM	HMDB
Verelan SR	HMDB
Veroptinstada	HMDB
Verpamil	HMDB
Vetrimil	HMDB
Vortac	HMDB
Dexverapamil	HMDB
Hydrochloride, verapamil	HMDB
Sandoz brand OF verapamil	HMDB
Verapamil hydrochloride	HMDB
Verapamil sandoz brand	HMDB

Chemical Formula

C₂₇H₃₈N₂O₄

Average Molecular Weight

454.6016

Monoisotopic Molecular Weight

454.283157714

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

Traditional Name

veraβ

CAS Registry Number

52-53-9

SMILES

COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

InChI Identifier

InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3

InChI Key

SGTNSNPWRIOYBX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Dimethoxybenzene
O-dimethoxybenzene
Phenethylamine
Phenylpropane
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Tertiary aliphatic amine
Tertiary amine
Nitrile
Carbonitrile
Ether
Organic oxygen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:77733 )
aromatic ether (CHEBI:77733 )
nitrile (CHEBI:77733 )
polyether (CHEBI:77733 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0242222)

Tissue

Connective tissue

Adipose tissue (HMDB: HMDB0242222)

Cell

Fibroblasts (HMDB: HMDB0242222)
Neuron (HMDB: HMDB0242222)

Hematocyte

Platelet (HMDB: HMDB0242222)

Organ

Stratum Corneum (HMDB: HMDB0242222)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	PhysProp
Boiling Point	243-246 °C at 1.00E-02 mm Hg	PhysProp
Water Solubility	4.47 mg/L	Not Available
LogP	3.79	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	210.2	30932474
[M+H]+	McLean	208.74	30932474
[M+H]+	Not Available	208.913	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000772

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	5.23	ALOGPS
logP	5.04	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.95 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	132.65 m³·mol⁻¹	ChemAxon
Polarizability	51.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	207.345	31661259
DarkChem	[M-H]-	206.748	31661259
AllCCS	[M+H]+	214.793	32859911
AllCCS	[M-H]-	215.593	32859911
DeepCCS	[M+H]+	214.888	30932474
DeepCCS	[M-H]-	212.53	30932474
DeepCCS	[M-2H]-	245.78	30932474
DeepCCS	[M+Na]+	221.008	30932474
AllCCS	[M+H]+	214.8	32859911
AllCCS	[M+H-H2O]+	212.7	32859911
AllCCS	[M+NH4]+	216.7	32859911
AllCCS	[M+Na]+	217.3	32859911
AllCCS	[M-H]-	215.6	32859911
AllCCS	[M+Na-2H]-	217.2	32859911
AllCCS	[M+HCOO]-	219.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Verapamil	COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3582.1	Standard polar	33892256
Verapamil	COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3106.0	Standard non polar	33892256
Verapamil	COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3165.8	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 - Verapamil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0cdu-4391500000-cd36ebd65bc8c7765961	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verapamil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-3519000000-b5e0b9e0caac5cb57222	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 - Verapamil Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004l-0702900000-6a46ea2d5eed6d8b01eb	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-4109800000-80d342090a0be3344e82	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-054w-0954400000-2def387c7c93ab211423	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0a4i-0000900000-4cde9a4b3a4f83d16afc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0a4i-0000900000-980b47834e505d54a0e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-066r-0902800000-ae024239c46b33917426	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-014i-0901000000-81d1159b3102cff76218	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-014i-0900000000-d9c344fee7b45b4030e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0gb9-0914000000-070bdb975910e9aae99c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-03di-0390000000-f41d80462c5d06c4f001	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0097-2980000000-9a2ab0bcab33f7eaac6b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0uxr-0900000000-252a9989a8511cb2db80	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0f79-0900000000-4fd6ca2c6c19c3bbf8f0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000900000-4365a47b2dc2f86bb272	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000900000-e6a2b357160bf5b92c22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOF	splash10-066r-0902400000-d8eac2ccd0a767c7e432	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOF	splash10-014i-0901000000-688f3c2345c5d9ccb8a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-QTOF , positive-QTOF	splash10-014i-0900000000-cd09f8a2be876936f662	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Verapamil LC-ESI-ITFT , positive-QTOF	splash10-0uxr-0918000000-76641dd6dbc5cb05e79a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 10V, Positive-QTOF	splash10-0a4i-0010900000-c5883de78bb084688acb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 20V, Positive-QTOF	splash10-014i-0573900000-c95a634d7e2ecac924b7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 40V, Positive-QTOF	splash10-014i-1962200000-5e5b0f3f1481cfd4da52	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 10V, Negative-QTOF	splash10-0udi-0000900000-44ab3d7fdbe57d5f189d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 20V, Negative-QTOF	splash10-0f79-0031900000-562635f25a21f2cbad9f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verapamil 40V, Negative-QTOF	splash10-0080-0192300000-aada67fc0f3e7f227e44	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Bladder
Brain
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Verapamil 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 DB00661	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00661	21059682	details

Abnormal Concentrations

Not Available

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

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00661

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022708

KNApSAcK ID

Not Available

Chemspider ID

2425

KEGG Compound ID

C07188

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verapamil

METLIN ID

3009

PubChem Compound

2520

PDB ID

Not Available

ChEBI ID

77733

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

Takeda H, Yamazaki Y, Akahane M, Igawa Y, Ajisawa Y, Nishizawa O: Role of the beta(3)-adrenoceptor in urine storage in the rat: comparison between the selective beta(3)-adrenoceptor agonist, CL316, 243, and various smooth muscle relaxants. J Pharmacol Exp Ther. 2000 Jun;293(3):939-45. [PubMed:10869395 ]
Wang YH, Jones DR, Hall SD: Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71. Epub 2005 Feb 2. [PubMed:15689501 ]
Byerly WG, Hartmann A, Foster DE, Tannenbaum AK: Verapamil in the treatment of maternal paroxysmal supraventricular tachycardia. Ann Emerg Med. 1991 May;20(5):552-4. [PubMed:2024796 ]
Miller MR, Withers R, Bhamra R, Holt DW: Verapamil and breast-feeding. Eur J Clin Pharmacol. 1986;30(1):125-6. [PubMed:3709626 ]
Takano A, Kusuhara H, Suhara T, Ieiri I, Morimoto T, Lee YJ, Maeda J, Ikoma Y, Ito H, Suzuki K, Sugiyama Y: Evaluation of in vivo P-glycoprotein function at the blood-brain barrier among MDR1 gene polymorphisms by using 11C-verapamil. J Nucl Med. 2006 Sep;47(9):1427-33. [PubMed:16954549 ]
Fakih H, MacLusky N, DeCherney A, Wallimann T, Huszar G: Enhancement of human sperm motility and velocity in vitro: effects of calcium and creatine phosphate. Fertil Steril. 1986 Nov;46(5):938-44. [PubMed:3781011 ]
Suzuki S, Nishimaki-Mogami T, Tamehiro N, Inoue K, Arakawa R, Abe-Dohmae S, Tanaka AR, Ueda K, Yokoyama S: Verapamil increases the apolipoprotein-mediated release of cellular cholesterol by induction of ABCA1 expression via Liver X receptor-independent mechanism. Arterioscler Thromb Vasc Biol. 2004 Mar;24(3):519-25. Epub 2004 Jan 15. [PubMed:14726413 ]
Glusa E: Effect of verapamil on platelet aggregation. Folia Haematol Int Mag Klin Morphol Blutforsch. 1988;115(4):469-73. [PubMed:2465955 ]
Ceccato A, Chiap P, Hubert P, Toussaint B, Crommen J: Automated determination of verapamil and norverapamil in human plasma with on-line coupling of dialysis to high-performance liquid chromatography and fluorometric detection. J Chromatogr A. 1996 Oct 25;750(1-2):351-60. [PubMed:8938391 ]
Nanni G, Panocchia N, Tacchino R, Foco M, Piccioni E, Castagneto M: Increased incidence of infection in verapamil-treated kidney transplant recipients. Transplant Proc. 2000 May;32(3):551-3. [PubMed:10812109 ]
Affolter H, Burkard WP, Pletscher A: Verapamil, an antagonist at 5-hydroxytryptamine receptors of human blood platelets. Eur J Pharmacol. 1985 Jan 22;108(2):157-62. [PubMed:3156755 ]
Rumiantsev DO, Piotrovskii VK, Riabokon' OS, Metelitsa VI: [Comparison of the verapamil concentration of human blood serum and saliva]. Farmakol Toksikol. 1987 Jan-Feb;50(1):85-9. [PubMed:3556560 ]
Gramatte T, Oertel R: Intestinal secretion of intravenous talinolol is inhibited by luminal R-verapamil. Clin Pharmacol Ther. 1999 Sep;66(3):239-45. [PubMed:10511059 ]
Hsiao P, Sasongko L, Link JM, Mankoff DA, Muzi M, Collier AC, Unadkat JD: Verapamil P-glycoprotein transport across the rat blood-brain barrier: cyclosporine, a concentration inhibition analysis, and comparison with human data. J Pharmacol Exp Ther. 2006 May;317(2):704-10. Epub 2006 Jan 13. [PubMed:16415090 ]
von Richter O, Greiner B, Fromm MF, Fraser R, Omari T, Barclay ML, Dent J, Somogyi AA, Eichelbaum M: Determination of in vivo absorption, metabolism, and transport of drugs by the human intestinal wall and liver with a novel perfusion technique. Clin Pharmacol Ther. 2001 Sep;70(3):217-27. [PubMed:11557909 ]
Narang PK, Blumhardt CL, Doran AR, Pickar D: Steady-state cerebrospinal fluid transfer of verapamil and metabolites in patients with schizophrenia. Clin Pharmacol Ther. 1988 Nov;44(5):550-7. [PubMed:3180637 ]
Szymanski W, Skublicki S, Jankowski A, Kotzbach R: [Pharmacokinetic investigations of verapamil used as a concomitant drug in treatment of premature labor]. Ginekol Pol. 1992 Apr;63(4):166-71. [PubMed:1303922 ]
Wang YH, Jones DR, Hall SD: Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66. [PubMed:14744949 ]
Dumestre-Toulet V, Cirimele V, Gromb S, Belooussoff T, Lavault D, Ludes B, Kintz P: Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample. Forensic Sci Int. 2002 Mar 28;126(1):71-6. [PubMed:11955836 ]
Bauer LA, Horn JR, Maxon MS, Easterling TR, Shen DD, Strandness DE Jr: Effect of metoprolol and verapamil administered separately and concurrently after single doses on liver blood flow and drug disposition. J Clin Pharmacol. 2000 May;40(5):533-43. [PubMed:10806607 ]
Hofer CA, Smith JK, Tenholder MF: Verapamil intoxication: a literature review of overdoses and discussion of therapeutic options. Am J Med. 1993 Oct;95(4):431-8. [PubMed:8213877 ]
Bellamy WT: P-glycoproteins and multidrug resistance. Annu Rev Pharmacol Toxicol. 1996;36:161-83. [PubMed:8725386 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Enzyme Details

3. 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

Enzyme Details

4. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

Enzyme Details

5. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

Enzyme Details

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

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

Enzyme Details

7. ATP-sensitive inward rectifier potassium channel 11

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

Enzyme Details

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

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-1F 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:: CACNA1F
Uniprot ID:: O60840
Molecular weight:: 220675.9

Enzyme Details

9. Voltage-dependent T-type calcium channel subunit alpha-1G

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-1G gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by 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:: CACNA1G
Uniprot ID:: O43497
Molecular weight:: 262468.6

Enzyme Details

10. Voltage-dependent T-type calcium channel subunit alpha-1I

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. Isoform alpha-1I 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. Gates in voltage ranges similar to, but higher than alpha 1G or alpha 1H
Gene Name:: CACNA1I
Uniprot ID:: Q9P0X4
Molecular weight:: 245100.8

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for Verapamil (HMDB0001850)

MOL for HMDB0001850 (Verapamil)

3D MOL for HMDB0001850 (Verapamil)

3D SDF for HMDB0001850 (Verapamil)

3D-SDF for HMDB0001850 (Verapamil)

PDB for HMDB0001850 (Verapamil)

3D PDB for HMDB0001850 (Verapamil)

SMILES for HMDB0001850 (Verapamil)

INCHI for HMDB0001850 (Verapamil)

Structure for HMDB0001850 (Verapamil)

3D Structure for HMDB0001850 (Verapamil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Transporters