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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10)transporters (1) Show 11 proteins XML

enzymes (10)transporters (1) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015374

Secondary Accession Numbers

HMDB15374

Metabolite Identification

Common Name

Bepridil

Description

Bepridil is only found in individuals that have used or taken this drug. It is a long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist. [PubChem]Bepridil has inhibitory effects on both the slow calcium (L-type) and fast sodium inward currents in myocardial and vascular smooth muscle, interferes with calcium binding to calmodulin, and blocks both voltage and receptor operated calcium channels. Bepridil inhibits the transmembrane influx of calcium ions into cardiac and vascular smooth muscle. This has been demonstrated in isolated myocardial and vascular smooth muscle preparations in which both the slope of the calcium dose response curve and the maximum calcium-induced inotropic response were significantly reduced by bepridil. In cardiac myocytes in vitro, bepridil was shown to be tightly bound to actin. Bepridil regularly reduces heart rate and arterial pressure at rest and at a given level of exercise by dilating peripheral arterioles and reducing total peripheral resistance (afterload) against which the heart works.

Structure

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

1244
  Mrv0541 02231215212D          

 27 29  0  0  1  0            999 V2000
    5.2224   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087    1.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762    0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1157    1.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0015374
     RDKit          3D
Bepridil
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.1622    0.2793    0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.0776    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    0.5862   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    0.3806    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1076    0.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    0.5104    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    0.1717    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.8750   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.8006   -1.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743   -0.2650   -1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234   -0.8742   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806   -2.0770   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829   -2.6318    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2590   -1.9248    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506   -0.7111   -0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -0.1931   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    2.0859   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    2.7547   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    3.9944   -2.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1151    4.5099   -1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    3.8202   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743    2.5810   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -1.2431    0.7885 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -1.9640    2.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -3.2228    1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.9684    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -1.9042   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9876    0.2817    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4106   -0.4094    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0776    1.3161    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694   -1.1804    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7281    0.8048   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3241    1.5635   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677   -0.0433   -1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -0.0759    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    1.5030    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.6406    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697    0.1749    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    0.4824    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603    1.9803   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.5000   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642   -1.0560   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.0929   -2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798   -2.6678   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -3.5789    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1503   -2.2937    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3081   -0.1765   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.7727   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.3488   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    4.5218   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    5.4839   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    4.1657    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    2.0136    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -1.3648    2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -2.2667    2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720   -3.4994    2.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898   -4.1099    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -2.5908    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179   -3.8889    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -1.3381   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -2.5062   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 16 11  1  0
 22 17  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
M  END

1244
  Mrv0541 02231215212D          

 27 29  0  0  1  0            999 V2000
    5.2224   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087    1.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762    0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1157    1.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015374

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C24H34N2O/c1-21(2)19-27-20-24(25-15-9-10-16-25)18-26(23-13-7-4-8-14-23)17-22-11-5-3-6-12-22/h3-8,11-14,21,24H,9-10,15-20H2,1-2H3

> <INCHI_KEY>
UIEATEWHFDRYRU-UHFFFAOYSA-N

> <FORMULA>
C24H34N2O

> <MOLECULAR_WEIGHT>
366.5396

> <EXACT_MASS>
366.26711372

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.49593555275381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-N-[3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl]aniline

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.487299518666666

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.156553004146938

> <JCHEM_POLAR_SURFACE_AREA>
15.71

> <JCHEM_REFRACTIVITY>
115.11720000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bepridil

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015374
     RDKit          3D
Bepridil
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.1622    0.2793    0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.0776    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    0.5862   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    0.3806    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1076    0.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    0.5104    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    0.1717    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.8750   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.8006   -1.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743   -0.2650   -1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234   -0.8742   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806   -2.0770   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829   -2.6318    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2590   -1.9248    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506   -0.7111   -0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -0.1931   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    2.0859   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    2.7547   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    3.9944   -2.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1151    4.5099   -1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    3.8202   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743    2.5810   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -1.2431    0.7885 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -1.9640    2.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -3.2228    1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.9684    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -1.9042   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9876    0.2817    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4106   -0.4094    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0776    1.3161    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694   -1.1804    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7281    0.8048   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3241    1.5635   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677   -0.0433   -1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -0.0759    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    1.5030    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.6406    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697    0.1749    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    0.4824    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603    1.9803   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.5000   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642   -1.0560   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.0929   -2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798   -2.6678   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -3.5789    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1503   -2.2937    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3081   -0.1765   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.7727   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.3488   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    4.5218   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    5.4839   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    4.1657    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    2.0136    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -1.3648    2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -2.2667    2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720   -3.4994    2.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898   -4.1099    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -2.5908    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179   -3.8889    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -1.3381   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -2.5062   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 16 11  1  0
 22 17  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1244                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.748  -1.925   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.748   1.155   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748   0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.910   2.687   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.156   0.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.416   3.007   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.186   1.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082  -4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -5.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -3.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   3.465   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748   3.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -3.465   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.748  -4.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   5.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748   5.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414   5.775   0.000  0.00  0.00           C+0
CONECT    1   10   13                                                       
CONECT    2    4    5    6                                                  
CONECT    3    9   11   12                                                  
CONECT    4    2    9   10                                                  
CONECT    5    2    7                                                       
CONECT    6    2    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    3    4                                                       
CONECT   10    1    4                                                       
CONECT   11    3   15                                                       
CONECT   12    3   16   17                                                  
CONECT   13    1   14                                                       
CONECT   14   13   18   19                                                  
CONECT   15   11   20   21                                                  
CONECT   16   12   22                                                       
CONECT   17   12   23                                                       
CONECT   18   14                                                            
CONECT   19   14                                                            
CONECT   20   15   25                                                       
CONECT   21   15   26                                                       
CONECT   22   16   24                                                       
CONECT   23   17   24                                                       
CONECT   24   22   23                                                       
CONECT   25   20   27                                                       
CONECT   26   21   27                                                       
CONECT   27   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0015374
HETATM    1  C1  UNL     1      -6.162   0.279   0.885  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.825  -0.078   0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.763   0.586  -1.086  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.738   0.381   1.194  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.477   0.108   0.730  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.465   0.510   1.562  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.100   0.172   0.971  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.011   0.875  -0.324  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.214   0.801  -1.069  1.00  0.00           N  
HETATM   10  C8  UNL     1       1.874  -0.265  -1.744  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.023  -0.874  -1.034  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.981  -2.077  -0.382  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.083  -2.632   0.277  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.259  -1.925   0.262  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.351  -0.711  -0.382  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.251  -0.193  -1.020  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.909   2.086  -1.165  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.707   2.755  -2.352  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.336   3.994  -2.479  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.115   4.510  -1.463  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.302   3.820  -0.284  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.674   2.581  -0.154  1.00  0.00           C  
HETATM   23  N2  UNL     1       0.051  -1.243   0.789  1.00  0.00           N  
HETATM   24  C21 UNL     1       0.028  -1.964   2.049  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.753  -3.223   1.860  1.00  0.00           C  
HETATM   26  C23 UNL     1      -1.596  -2.968   0.634  1.00  0.00           C  
HETATM   27  C24 UNL     1      -0.809  -1.904  -0.110  1.00  0.00           C  
HETATM   28  H1  UNL     1      -6.988   0.282   0.129  1.00  0.00           H  
HETATM   29  H2  UNL     1      -6.411  -0.409   1.736  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.078   1.316   1.269  1.00  0.00           H  
HETATM   31  H4  UNL     1      -4.769  -1.180   0.098  1.00  0.00           H  
HETATM   32  H5  UNL     1      -3.728   0.805  -1.372  1.00  0.00           H  
HETATM   33  H6  UNL     1      -5.324   1.563  -1.103  1.00  0.00           H  
HETATM   34  H7  UNL     1      -5.268  -0.043  -1.856  1.00  0.00           H  
HETATM   35  H8  UNL     1      -3.946  -0.076   2.187  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.841   1.503   1.257  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.490   1.641   1.580  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.570   0.175   2.604  1.00  0.00           H  
HETATM   39  H12 UNL     1       0.661   0.482   1.714  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.260   1.980  -0.188  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.824   0.500  -1.018  1.00  0.00           H  
HETATM   42  H15 UNL     1       1.164  -1.056  -2.110  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.327   0.093  -2.734  1.00  0.00           H  
HETATM   44  H17 UNL     1       2.080  -2.668  -0.359  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.042  -3.579   0.789  1.00  0.00           H  
HETATM   46  H19 UNL     1       6.150  -2.294   0.751  1.00  0.00           H  
HETATM   47  H20 UNL     1       6.308  -0.177  -0.372  1.00  0.00           H  
HETATM   48  H21 UNL     1       4.366   0.773  -1.533  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.095   2.349  -3.148  1.00  0.00           H  
HETATM   50  H23 UNL     1       2.179   4.522  -3.410  1.00  0.00           H  
HETATM   51  H24 UNL     1       3.600   5.484  -1.583  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.896   4.166   0.547  1.00  0.00           H  
HETATM   53  H26 UNL     1       2.797   2.014   0.753  1.00  0.00           H  
HETATM   54  H27 UNL     1      -0.271  -1.365   2.907  1.00  0.00           H  
HETATM   55  H28 UNL     1       1.100  -2.267   2.246  1.00  0.00           H  
HETATM   56  H29 UNL     1      -1.372  -3.499   2.738  1.00  0.00           H  
HETATM   57  H30 UNL     1      -0.090  -4.110   1.658  1.00  0.00           H  
HETATM   58  H31 UNL     1      -2.586  -2.591   0.935  1.00  0.00           H  
HETATM   59  H32 UNL     1      -1.718  -3.889   0.014  1.00  0.00           H  
HETATM   60  H33 UNL     1      -1.517  -1.338  -0.697  1.00  0.00           H  
HETATM   61  H34 UNL     1      -0.195  -2.506  -0.857  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    4   31
CONECT    3   32   33   34
CONECT    4    5   35   36
CONECT    5    6
CONECT    6    7   37   38
CONECT    7    8   23   39
CONECT    8    9   40   41
CONECT    9   10   17
CONECT   10   11   42   43
CONECT   11   12   12   16
CONECT   12   13   44
CONECT   13   14   14   45
CONECT   14   15   46
CONECT   15   16   16   47
CONECT   16   48
CONECT   17   18   18   22
CONECT   18   19   49
CONECT   19   20   20   50
CONECT   20   21   51
CONECT   21   22   22   52
CONECT   22   53
CONECT   23   24   27
CONECT   24   25   54   55
CONECT   25   26   56   57
CONECT   26   27   58   59
CONECT   27   60   61
END

HMDB0015374
     RDKit          3D
Bepridil
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.1622    0.2793    0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250   -0.0776    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    0.5862   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    0.3806    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1076    0.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    0.5104    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    0.1717    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.8750   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.8006   -1.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743   -0.2650   -1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234   -0.8742   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806   -2.0770   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829   -2.6318    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2590   -1.9248    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506   -0.7111   -0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -0.1931   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    2.0859   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071    2.7547   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    3.9944   -2.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1151    4.5099   -1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    3.8202   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743    2.5810   -0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -1.2431    0.7885 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -1.9640    2.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -3.2228    1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.9684    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090   -1.9042   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9876    0.2817    0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4106   -0.4094    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0776    1.3161    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694   -1.1804    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7281    0.8048   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3241    1.5635   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2677   -0.0433   -1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -0.0759    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    1.5030    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.6406    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697    0.1749    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    0.4824    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603    1.9803   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    0.5000   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642   -1.0560   -2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.0929   -2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798   -2.6678   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -3.5789    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1503   -2.2937    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3081   -0.1765   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.7727   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.3488   -3.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    4.5218   -3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    5.4839   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    4.1657    0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    2.0136    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -1.3648    2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -2.2667    2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3720   -3.4994    2.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898   -4.1099    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -2.5908    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179   -3.8889    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -1.3381   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -2.5062   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 16 11  1  0
 22 17  1  0
 27 23  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bepadin	ChEBI
Bepridil, (+)-isomer	HMDB
Bepridil, alpha-isomer	HMDB
Monohydrochloride, bepridil	HMDB
Riom brand OF bepridil hydrochloride	HMDB
Vascor	HMDB
1978 CERM	HMDB
Bepridil monohydrochloride	HMDB
Bepridil monohydrochloride, monohydrate	HMDB
Bepridil monohydrochloride, alpha isomer	HMDB
Bepridil monohydrochloride, alpha-isomer	HMDB
Bepridil, (-)-isomer	HMDB
Bepridil, alpha isomer	HMDB
Cordium	HMDB
Wallace brand OF bepridil hydrochloride	HMDB
1978-CERM	HMDB
Bepridil, (+-)-isomer	HMDB
CERM-1978	HMDB
Bedapin	HMDB
CERM 1978	HMDB
Monohydrochloride, alpha-isomer bepridil	HMDB
Nourypharma brand OF bepridil hydrochloride	HMDB
Unicordium	HMDB

Chemical Formula

C₂₄H₃₄N₂O

Average Molecular Weight

366.5396

Monoisotopic Molecular Weight

366.26711372

IUPAC Name

N-benzyl-N-[3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl]aniline

Traditional Name

bepridil

CAS Registry Number

64706-54-3

SMILES

CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1

InChI Identifier

InChI=1S/C24H34N2O/c1-21(2)19-27-20-24(25-15-9-10-16-25)18-26(23-13-7-4-8-14-23)17-22-11-5-3-6-12-22/h3-8,11-14,21,24H,9-10,15-20H2,1-2H3

InChI Key

UIEATEWHFDRYRU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Benzylamine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:3061 )
pyrrolidines (CHEBI:3061 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015374)
Membrane (HMDB: HMDB0015374)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0066 g/L	Not Available
LogP	5.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	5.33	ALOGPS
logP	5.49	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.71 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.12 m³·mol⁻¹	ChemAxon
Polarizability	43.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.023	31661259
DarkChem	[M-H]-	186.138	31661259
DeepCCS	[M+H]+	185.411	30932474
DeepCCS	[M-H]-	183.053	30932474
DeepCCS	[M-2H]-	216.859	30932474
DeepCCS	[M+Na]+	192.204	30932474
AllCCS	[M+H]+	192.9	32859911
AllCCS	[M+H-H2O]+	190.3	32859911
AllCCS	[M+NH4]+	195.3	32859911
AllCCS	[M+Na]+	196.0	32859911
AllCCS	[M-H]-	193.0	32859911
AllCCS	[M+Na-2H]-	193.3	32859911
AllCCS	[M+HCOO]-	193.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bepridil	CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1	3349.7	Standard polar	33892256
Bepridil	CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1	2675.8	Standard non polar	33892256
Bepridil	CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1	2648.3	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 - Bepridil GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-8690000000-768d16d0b40d5b2932e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bepridil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bepridil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 10V, Positive-QTOF	splash10-066u-9327000000-af93fdc247abd705238e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 20V, Positive-QTOF	splash10-0006-9320000000-2b4cc0379d6875c5c1ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 40V, Positive-QTOF	splash10-052f-9000000000-675ce98f6b729bc83dba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 10V, Negative-QTOF	splash10-014i-2019000000-ad43d391dc0021d16521	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 20V, Negative-QTOF	splash10-05x0-8895000000-f6081c9498fdf024c130	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 40V, Negative-QTOF	splash10-00di-9220000000-a3433671009f66e28106	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 10V, Positive-QTOF	splash10-014i-1309000000-d08b70c49dbd9bec8ecc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 20V, Positive-QTOF	splash10-014l-9527000000-d456621f5de3ad386cb9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 40V, Positive-QTOF	splash10-0006-9400000000-94c75315da72259763c8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 10V, Negative-QTOF	splash10-014i-0219000000-f342a2f667dda5fca827	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 20V, Negative-QTOF	splash10-07vi-3629000000-ebc015e4f6668c377562	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bepridil 40V, Negative-QTOF	splash10-003r-9822000000-709fc32123a04540e60f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01244	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01244	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01244

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2261

KEGG Compound ID

C06847

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bepridil

METLIN ID

Not Available

PubChem Compound

2351

PDB ID

Not Available

ChEBI ID

3061

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

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Gene Name:: PDE1A
Uniprot ID:: P54750
Molecular weight:: 61251.38

References

Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]

Enzyme Details

2. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as a substrate.
Gene Name:: PDE1B
Uniprot ID:: Q01064
Molecular weight:: 61379.235

References

Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]

Enzyme Details

3. Sodium/potassium-transporting ATPase subunit alpha-1

General function:: Involved in ATP binding
Specific function:: This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:: ATP1A1
Uniprot ID:: P05023
Molecular weight:: 112895.01

References

Kovacic H, Gallice P, Crevat A: Inhibition of sodium pump by bepridil. An in vitro and microcalorimetric study. Biochem Pharmacol. 1992 Oct 20;44(8):1529-34. [PubMed:1329768 ]
Raess BU, Record DM: Inhibition of erythrocyte Ca2(+)-pump by Ca2+ antagonists. Biochem Pharmacol. 1990 Dec 1;40(11):2549-55. [PubMed:2148481 ]
Smith SJ, England PJ: The effects of reported Ca2+ sensitisers on the rates of Ca2+ release from cardiac troponin C and the troponin-tropomyosin complex. Br J Pharmacol. 1990 Aug;100(4):779-85. [PubMed:2207500 ]
Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]
Fuchs J, Mainka L, Reifart N, Zimmer G: Effects of bepridil on heart mitochondrial membrane and the isolated rat heart preparation. Arzneimittelforschung. 1986 Feb;36(2):209-12. [PubMed:2938592 ]

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. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]
Lamers JM, Verdouw PD, Mas-Oliva J: The effects of felodipine and bepridil on calcium-stimulated calmodulin binding and calcium pumping ATPase of cardiac sarcolemma before and after removal of endogenous calmodulin. Mol Cell Biochem. 1987 Dec;78(2):169-76. [PubMed:2964559 ]

Enzyme Details

6. Potassium voltage-gated channel subfamily KQT member 1

General function:: Involved in ion channel activity
Specific function:: Probably important in cardiac repolarization. Associates with KCNE1 (MinK) to form the I(Ks) cardiac potassium current. Elicits a rapidly activating, potassium-selective outward current. Muscarinic agonist oxotremorine-M strongly suppresses KCNQ1/KCNE1 current in CHO cells in which cloned KCNQ1/KCNE1 channels were coexpressed with M1 muscarinic receptors. May associate also with KCNE3 (MiRP2) to form the potassium channel that is important for cyclic AMP-stimulated intestinal secretion of chloride ions, which is reduced in cystic fibrosis and pathologically stimulated in cholera and other forms of secretory diarrhea
Gene Name:: KCNQ1
Uniprot ID:: P51787
Molecular weight:: 74697.9

References

Chouabe C, Drici MD, Romey G, Barhanin J: Effects of calcium channel blockers on cloned cardiac K+ channels IKr and IKs. Therapie. 2000 Jan-Feb;55(1):195-202. [PubMed:10860024 ]
Yumoto Y, Horie M, Kubota T, Ninomiya T, Kobori A, Takenaka K, Takano M, Niwano S, Izumi T: Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock. J Cardiovasc Pharmacol. 2004 Feb;43(2):178-82. [PubMed:14716203 ]
Chouabe C, Drici MD, Romey G, Barhanin J, Lazdunski M: HERG and KvLQT1/IsK, the cardiac K+ channels involved in long QT syndromes, are targets for calcium channel blockers. Mol Pharmacol. 1998 Oct;54(4):695-703. [PubMed:9765513 ]

Enzyme Details

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

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

References

Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
Bezprozvanny I, Tsien RW: Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967). Mol Pharmacol. 1995 Sep;48(3):540-9. [PubMed:7565636 ]

Enzyme Details

8. Voltage-dependent P/Q-type calcium channel subunit alpha-1A

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-1A gives rise to P and/or Q-type calcium currents. P/Q-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by the funnel toxin (Ftx) and by the omega-agatoxin- IVA (omega-Aga-IVA). They are however insensitive to dihydropyridines (DHP), and omega-conotoxin-GVIA (omega-CTx-GVIA)
Gene Name:: CACNA1A
Uniprot ID:: O00555
Molecular weight:: 282362.4

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 ]
Bezprozvanny I, Tsien RW: Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967). Mol Pharmacol. 1995 Sep;48(3):540-9. [PubMed:7565636 ]

Enzyme Details

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

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1H gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by nickel and mibefradil. A particularity of this type of channels is an opening at quite negative potentials, and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes
Gene Name:: CACNA1H
Uniprot ID:: O95180
Molecular weight:: 259160.2

References

Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
Bezprozvanny I, Tsien RW: Voltage-dependent blockade of diverse types of voltage-gated Ca2+ channels expressed in Xenopus oocytes by the Ca2+ channel antagonist mibefradil (Ro 40-5967). Mol Pharmacol. 1995 Sep;48(3):540-9. [PubMed:7565636 ]

Enzyme Details

10. Troponin C, slow skeletal and cardiac muscles

General function:: Involved in calcium ion binding
Specific function:: Troponin is the central regulatory protein of striated muscle contraction. Tn consists of three components:Tn-I which is the inhibitor of actomyosin ATPase, Tn-T which contains the binding site for tropomyosin and Tn-C. The binding of calcium to Tn-C abolishes the inhibitory action of Tn on actin filaments
Gene Name:: TNNC1
Uniprot ID:: P63316
Molecular weight:: 18402.4

References

Abusamhadneh E, Abbott MB, Dvoretsky A, Finley N, Sasi S, Rosevear PR: Interaction of bepridil with the cardiac troponin C/troponin I complex. FEBS Lett. 2001 Sep 28;506(1):51-4. [PubMed:11591369 ]
Wang X, Li MX, Sykes BD: Structure of the regulatory N-domain of human cardiac troponin C in complex with human cardiac troponin I147-163 and bepridil. J Biol Chem. 2002 Aug 23;277(34):31124-33. Epub 2002 Jun 11. [PubMed:12060657 ]
MacLachlan LK, Reid DG, Mitchell RC, Salter CJ, Smith SJ: Binding of a calcium sensitizer, bepridil, to cardiac troponin C. A fluorescence stopped-flow kinetic, circular dichroism, and proton nuclear magnetic resonance study. J Biol Chem. 1990 Jun 15;265(17):9764-70. [PubMed:2351672 ]
Kleerekoper Q, Liu W, Choi D, Putkey JA: Identification of binding sites for bepridil and trifluoperazine on cardiac troponin C. J Biol Chem. 1998 Apr 3;273(14):8153-60. [PubMed:9525919 ]

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

Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465 ]

Only showing the first 10 proteins. There are 11 proteins in total.

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Showing metabocard for Bepridil (HMDB0015374)

MOL for HMDB0015374 (Bepridil)

3D MOL for HMDB0015374 (Bepridil)

3D SDF for HMDB0015374 (Bepridil)

3D-SDF for HMDB0015374 (Bepridil)

PDB for HMDB0015374 (Bepridil)

3D PDB for HMDB0015374 (Bepridil)

SMILES for HMDB0015374 (Bepridil)

INCHI for HMDB0015374 (Bepridil)

Structure for HMDB0015374 (Bepridil)

3D Structure for HMDB0015374 (Bepridil)

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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