4-Chloro-8-oxa-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,5-triene-6-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

ID: ALA174020

Cas Number: 141979-78-4

PubChem CID: 15171289

Max Phase: Preclinical

Molecular Formula: C20H25ClN2O2

Molecular Weight: 360.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CN2CCC1CC2)c1cc(Cl)cc2c1O[C@@H]1CCC[C@H]2C1

Standard InChI:  InChI=1S/C20H25ClN2O2/c21-14-9-16-13-2-1-3-15(8-13)25-19(16)17(10-14)20(24)22-18-11-23-6-4-12(18)5-7-23/h9-10,12-13,15,18H,1-8,11H2,(H,22,24)/t13-,15+,18+/m0/s1

Standard InChI Key:  ZIAMDRHEQRSMSY-JCKWVBRZSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  1  0  0  0  0  0999 V2000
    1.8417   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -2.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -3.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -0.2000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -3.9417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -0.2875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -3.2875    0.0000 H   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  2  1  0
  6  3  1  0
  7  6  1  0
  8  4  1  0
  9 11  1  0
 10  1  2  0
 11  7  1  0
 12 17  2  0
 13  3  2  0
 14  7  1  0
 15 16  1  0
 16  5  1  0
 17 10  1  0
 18 14  1  0
 19 14  1  0
 20 18  1  0
 21 19  1  0
 22 17  1  0
 23  8  1  0
 24 25  1  0
 25 16  1  0
  7 26  1  1
  8 27  1  6
 16 28  1  6
 12  4  1  0
 15  8  1  0
 23 24  1  0
  9 21  1  0
 20  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA174020

   (1S,9R)-N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-4-chloro-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-6-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: 360.89

Molecular Weight (Monoisotopic): 360.1605

AlogP: 3.58

#Rotatable Bonds: 2

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 7.75

CX LogP: 3.12

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: 0.15

References

1. Youssefyeh RD, Campbell HF, Airey JE, Klein S, Schnapper M, Powers M, Woodward R, Rodriguez W, Golec S, Studt W..  (1992)  Development of high-affinity 5-HT3 receptor antagonists. 2. Two novel tricyclic benzamides.,  35  (5): [PMID:1548679] [10.1021/jm00083a015]

Source

Source(1):

• Scientific Literature