2-Chloro-6,7,8,9-tetrahydro-dibenzofuran-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

ID: ALA174195

PubChem CID: 15171296

Max Phase: Preclinical

Molecular Formula: C20H23ClN2O2

Molecular Weight: 358.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CN2CCC1CC2)c1cc(Cl)cc2c3c(oc12)CCCC3

Standard InChI:  InChI=1S/C20H23ClN2O2/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/h9-10,12,17H,1-8,11H2,(H,22,24)

Standard InChI Key:  IRZRAMWZPYYODF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    2.3417   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -0.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -1.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500    0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000   -0.4542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -4.4125    0.0000 C   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  3  1  0
  7  4  1  0
  8  5  1  0
  9  8  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  6  1  0
 23  7  1  0
 24 22  1  0
 25 23  1  0
  7  6  2  0
 11 16  1  0
 24 25  1  0
 20 10  1  0
 10 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA174195

   N-(1-azabicyclo[2.2.2]octan-3-yl)-2-chloro-6,7,8,9-tetrahydrodibenzofuran-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: 358.87

Molecular Weight (Monoisotopic): 358.1448

AlogP: 3.79

#Rotatable Bonds: 2

Polar Surface Area: 45.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.90

CX LogP: 3.40

CX LogD: 2.78

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -0.54

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