(1S,9S)-N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-4-chloro-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-6-carboxamide

ID: ALA366617

Cas Number: 136174-04-4

PubChem CID: 9800933

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]1CCCC[C@@H]21

Standard InChI:  InChI=1S/C20H25ClN2O2/c21-13-9-15-14-3-1-2-4-18(14)25-19(15)16(10-13)20(24)22-17-11-23-7-5-12(17)6-8-23/h9-10,12,14,17-18H,1-8,11H2,(H,22,24)/t14-,17+,18-/m0/s1

Standard InChI Key:  LDYMIBZOCSHLBG-QGTPRVQTSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  1  0  0  0  0  0999 V2000
    4.2375   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -4.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -6.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -6.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -1.7292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.0167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -3.2417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000   -1.1542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  1  0
  6  5  1  0
  7  3  1  0
  8  4  1  0
  9  6  1  0
 10 13  1  0
 11  2  2  0
 12  3  1  0
 13  9  1  0
 14  5  2  0
 15  9  1  0
 16 12  2  0
 17 15  1  0
 18 15  1  0
 19 17  1  0
 20 18  1  0
 21 16  1  0
 22  7  1  0
 23  8  1  0
 24 22  1  0
 25 23  1  0
  9 26  1  1
  8 27  1  1
  7 28  1  1
  8  7  1  0
 11 16  1  0
 24 25  1  0
 10 20  1  0
 19 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA366617

   4-Dibenzofurancarboxamide, N-1-azabicyclo(2.2.2)oct-3-yl-2-chloro-5a,6,7,8,9,9a-hexahydro-, (5aS-(4(R*),5aalpha,9aalpha))-

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: 13.81

CX Basic pKa: 7.74

CX LogP: 3.19

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: 0.03

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