1-[3-((R)-1-Methyl-pyrrolidin-2-ylmethyl)-1H-indol-5-yl]-1H-benzoimidazole-5-carbonitrile

ID: ALA75642

PubChem CID: 9950538

Max Phase: Preclinical

Molecular Formula: C22H21N5

Molecular Weight: 355.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CP-161242 | CHEMBL75642|CP-161242|SCHEMBL7448014|BDBM50285522|1-[3-((R)-1-Methyl-pyrrolidin-2-ylmethyl)-1H-indol-5-yl]-1H-benzoimidazole-5-carbonitrile

Canonical SMILES:  CN1CCC[C@@H]1Cc1c[nH]c2ccc(-n3cnc4cc(C#N)ccc43)cc12

Standard InChI:  InChI=1S/C22H21N5/c1-26-8-2-3-17(26)10-16-13-24-20-6-5-18(11-19(16)20)27-14-25-21-9-15(12-23)4-7-22(21)27/h4-7,9,11,13-14,17,24H,2-3,8,10H2,1H3/t17-/m1/s1

Standard InChI Key:  KVKYGVOAHGNAKZ-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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   -0.2191   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -1.4036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294   -1.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107   -0.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -2.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4538   -3.2774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392   -1.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9289   -2.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7979   -0.2023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775   -1.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    2.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6742   -3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4741   -0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003   -0.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2494   -3.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -3.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1065    0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8980    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -0.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724    0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0966   -1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760   -0.3817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  6  1  0
  5  1  1  0
  6 10  1  0
  7  5  2  0
  8  1  1  0
  9 15  1  0
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 11  4  2  0
 12 16  1  0
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 14 17  3  0
 15 21  1  0
 16 13  1  0
 17 22  1  0
 18  5  1  0
 19  7  1  0
 20  8  1  0
 21 20  2  0
 22 23  1  0
 23 18  2  0
 24 12  1  0
 25 12  1  0
 26 27  1  0
 27 16  1  0
 16 28  1  1
  7  3  1  0
  6 15  2  0
 22 19  2  0
  9 11  1  0
 26 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA75642

   1-[3-((R)-1-Methyl-pyrrolidin-2-ylmethyl)-1H-indol-5-yl]-1H-benzoimidazole-5-carbonitrile

Molecule Features

Natural Product: No

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: 355.45

Molecular Weight (Monoisotopic): 355.1797

AlogP: 4.02

#Rotatable Bonds: 3

Polar Surface Area: 60.64

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.87

CX LogP: 3.79

CX LogD: 1.36

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -1.16

References

1. Macor JE, Blank DH, Desai K, Fox CB, Kenneth Koe B, Lebel LA, Post RJ, Schmidt AW, Schulz DW, Seymour PA.  (1995)  5-cyano-1-[3-(N-methylpyrrolidin-2R-ylmethyl)indol-5-yl] benzimidazole (CP-161,242): A potent, centrally active 5-HT1D receptor agonist and benzodiazepine partial agonist,  5  (20): [10.1016/0960-894X(95)00417-R]

2. Macor JE, Blake JF, Desai K, Post RJ, Schmidt AW.  (1995)  The discovery of a novel and potent benzodiazepine receptor pharmacophore,  5  (20): [10.1016/0960-894X(95)00418-S]

Source

Source(1):

• Scientific Literature