[2-(5-Imidazo[4,5-b]pyridin-3-yl-1H-indol-3-yl)-ethyl]-dimethyl-amine

ID: ALA80189

PubChem CID: 11722647

Max Phase: Preclinical

Molecular Formula: C18H19N5

Molecular Weight: 305.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCc1c[nH]c2ccc(-n3cnc4cccnc43)cc12

Standard InChI:  InChI=1S/C18H19N5/c1-22(2)9-7-13-11-20-16-6-5-14(10-15(13)16)23-12-21-17-4-3-8-19-18(17)23/h3-6,8,10-12,20H,7,9H2,1-2H3

Standard InChI Key:  SZSNAHWJFCIUBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.8333   -0.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1125    0.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6458    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375    2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  1  1  0
  6  8  1  0
  7 12  1  0
  8  5  2  0
  9  6  1  0
 10  9  2  0
 11  3  2  0
 12 16  1  0
 13  3  1  0
 14  5  1  0
 15  9  1  0
 16 14  2  0
 17 18  1  0
 18 15  1  0
 19 13  2  0
 20 11  1  0
 21 17  1  0
 22 17  1  0
 23 19  1  0
 11  4  1  0
  6 12  2  0
 23 20  2  0
  7 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA80189

   [2-(5-Imidazo[4,5-b]pyridin-3-yl-1H-indol-3-yl)-ethyl]-dimethyl-amine

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: 305.39

Molecular Weight (Monoisotopic): 305.1640

AlogP: 3.01

#Rotatable Bonds: 4

Polar Surface Area: 49.74

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.54

CX LogP: 2.62

CX LogD: 0.49

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: -1.12

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