2-Chloro-5a,6,7,8,9,9a-hexahydro-dibenzofuran-4-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

ID: ALA171640

PubChem CID: 44383619

Max Phase: Preclinical

Molecular Formula: C19H25ClN2O3

Molecular Weight: 364.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCN1CCOCC1)c1cc(Cl)cc2c1OC1CCCCC21

Standard InChI:  InChI=1S/C19H25ClN2O3/c20-13-11-15-14-3-1-2-4-17(14)25-18(15)16(12-13)19(23)21-5-6-22-7-9-24-10-8-22/h11-12,14,17H,1-10H2,(H,21,23)

Standard InChI Key:  IQRVVSJZXLQUGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  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
    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
    5.9042   -0.4375    0.0000 N   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
    3.0500    0.3750    0.0000 O   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
    7.3375    0.3833    0.0000 O   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
    4.4792   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.8542    0.0000 C   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
    6.6292   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042    0.3833    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
    6.6167    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375   -0.4417    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  2  2  0
  9  3  1  0
 10 17  1  0
 11  9  2  0
 12  5  2  0
 13  5  1  0
 14 22  1  0
 15 11  1  0
 16 13  1  0
 17 16  1  0
 18  6  1  0
 19 10  1  0
 20 10  1  0
 21  7  1  0
 22 20  1  0
 23 19  1  0
 24 18  1  0
 25 21  1  0
  7  6  1  0
  8 11  1  0
 24 25  1  0
 23 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA171640

   2-chloro-N-(2-morpholin-4-ylethyl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-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: 364.87

Molecular Weight (Monoisotopic): 364.1554

AlogP: 2.82

#Rotatable Bonds: 4

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: 5.90

CX LogP: 2.62

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -0.90

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