5-Methoxy-1H-indole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

ID: ALA356567

PubChem CID: 15681420

Max Phase: Preclinical

Molecular Formula: C17H21N3O2

Molecular Weight: 299.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]ccc2c1C(=O)NC1CN2CCC1CC2

Standard InChI:  InChI=1S/C17H21N3O2/c1-22-15-3-2-13-12(4-7-18-13)16(15)17(21)19-14-10-20-8-5-11(14)6-9-20/h2-4,7,11,14,18H,5-6,8-10H2,1H3,(H,19,21)

Standard InChI Key:  HMOMXYPGOQVVIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.2625   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -2.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -6.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -2.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -2.5292    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  3  1  0
  6 11  1  0
  7  8  1  0
  8  4  1  0
  9  2  1  0
 10 13  2  0
 11  5  1  0
 12  1  2  0
 13  4  1  0
 14  5  1  0
 15 16  1  0
 16  9  2  0
 17 14  1  0
 18 14  1  0
 19 17  1  0
 20 18  1  0
 21  9  1  0
 22 21  1  0
 15  8  2  0
 10  7  1  0
 20  6  1  0
 19  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA356567

   N-(1-azabicyclo[2.2.2]octan-3-yl)-5-methoxy-1H-indole-4-carboxamide

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: 299.37

Molecular Weight (Monoisotopic): 299.1634

AlogP: 2.00

#Rotatable Bonds: 3

Polar Surface Area: 57.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.90

CX LogP: 1.36

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: -0.25

References

1. Blum E, Buchheit K, Buescher H, Gamse R, Kloeppner E, Meigel H, Papageorgiou C, Waelchli R, Revesz L.  (1992)  Design and synthesis of novel ligands for the 5-HT3 and the 5-HT4 receptor,  2  (5): [10.1016/S0960-894X(00)80170-5]

Source

Source(1):

• Scientific Literature