2-Chloro-5a,6,7,8,9,9a-hexahydro-dibenzofuran-4-carboxylic acid [2-(1-methyl-1H-pyrrol-2-yl)-ethyl]-amide

ID: ALA369275

PubChem CID: 44383516

Max Phase: Preclinical

Molecular Formula: C20H23ClN2O2

Molecular Weight: 358.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cccc1CCNC(=O)c1cc(Cl)cc2c1OC1CCCCC21

Standard InChI:  InChI=1S/C20H23ClN2O2/c1-23-10-4-5-14(23)8-9-22-20(24)17-12-13(21)11-16-15-6-2-3-7-18(15)25-19(16)17/h4-5,10-12,15,18H,2-3,6-9H2,1H3,(H,22,24)

Standard InChI Key:  MXIABTDFHLAMNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.5792   -6.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -6.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -7.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9000   -5.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -6.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0292   -3.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -4.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -5.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -5.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750   -6.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -8.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -8.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -8.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -8.9542    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  9  1  0
  8  4  1  0
  9 18  1  0
 10  2  2  0
 11  3  1  0
 12  7  1  0
 13 14  1  0
 14  9  2  0
 15 11  2  0
 16  5  2  0
 17  5  1  0
 18 20  1  0
 19 15  1  0
 20 17  1  0
 21  7  1  0
 22  6  1  0
 23  8  1  0
 24 22  1  0
 25 23  1  0
  8  6  1  0
 10 15  1  0
 24 25  1  0
 12 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA369275

   2-chloro-N-[2-(1-methylpyrrol-2-yl)ethyl]-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: 358.87

Molecular Weight (Monoisotopic): 358.1448

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 43.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.72

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -0.62

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