Devapamil

ID: ALA2074792

Cas Number: 92302-55-1

PubChem CID: 65832

Max Phase: Phase

Molecular Formula: C26H36N2O3

Molecular Weight: 424.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Desmethoxyverapamil | D 888 | Devapamil|92302-55-1|Devapamil [INN]|Devapamilum|Devapamilo|Desmethoxyverapamil|(+/-)-Devapamil|2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-((m-methoxyphenethyl)methylamino)valeronitrile|M6142PTV7J|CHEBI:34673|2-(3,4-dimethoxyphenyl)-5-[2-(3-methoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile|D 888; Desmethoxyverapamil; Devapamil|D 888|Devapamilum [Latin]|Devapamilo [Spanish]|2-(3,4-dimethoxyphenyl)-2-isopropyl-5-{[2-(3-methoxyphenyl)ethyl](methyl)amino}pentaneniShow More⌵

Canonical SMILES:  COc1cccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)c1

Standard InChI:  InChI=1S/C26H36N2O3/c1-20(2)26(19-27,22-11-12-24(30-5)25(18-22)31-6)14-8-15-28(3)16-13-21-9-7-10-23(17-21)29-4/h7,9-12,17-18,20H,8,13-16H2,1-6H3

Standard InChI Key:  VMVKIDPOEOLUFS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
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   -1.8458   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191    1.1137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1000   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    1.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542    1.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292    2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000    2.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  3  0
  5  2  1  0
  6  5  2  0
  7  9  2  0
  8  2  2  0
  9  8  1  0
 10  1  1  0
 11 23  1  0
 12 13  2  0
 13 17  1  0
 14  6  1  0
 15 11  1  0
 16 12  1  0
 17 15  1  0
 18  1  1  0
 19  7  1  0
 20 16  1  0
 21 18  1  0
 22 24  2  0
 23 21  1  0
 24 13  1  0
 25 22  1  0
 26 11  1  0
 27 10  1  0
 28 10  1  0
 29 14  1  0
 30 19  1  0
 31 20  1  0
  6  7  1  0
 16 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074792

   DEVAPAMIL

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.59

Molecular Weight (Monoisotopic): 424.2726

AlogP: 5.08

#Rotatable Bonds: 12

Polar Surface Area: 54.72

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.69

CX LogP: 5.20

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.24

References

1. Höllt V, Kouba M, Dietel M, Vogt G..  (1992)  Stereoisomers of calcium antagonists which differ markedly in their potencies as calcium blockers are equally effective in modulating drug transport by P-glycoprotein.,  43  (1): [PMID:1352973] [10.1016/0006-2952(92)90149-d]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database