N-(6-Chloro-9H-beta-carbolin-8-yl)-4-methoxy-benzamide

ID: ALA78885

PubChem CID: 21362748

Max Phase: Preclinical

Molecular Formula: C19H14ClN3O2

Molecular Weight: 351.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)Nc2cc(Cl)cc3c4cc[nH]cc-4nc23)cc1

Standard InChI:  InChI=1S/C19H14ClN3O2/c1-25-13-4-2-11(3-5-13)19(24)23-16-9-12(20)8-15-14-6-7-21-10-17(14)22-18(15)16/h2-10,21H,1H3,(H,23,24)

Standard InChI Key:  VGRCMUSKMRUWMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    2.0792   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -0.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -2.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    0.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292    1.5208    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958    0.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  2  1  0
  7  3  2  0
  8  5  1  0
  9  4  2  0
 10  3  1  0
 11  8  1  0
 12  9  1  0
 13  8  2  0
 14 17  1  0
 15 11  2  0
 16 11  1  0
 17  6  2  0
 18 12  1  0
 19 20  1  0
 20 16  2  0
 21 15  1  0
 22  7  1  0
 23 19  1  0
 24 22  2  0
 25 23  1  0
  7  6  1  0
 10 12  2  0
 14 24  1  0
 21 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA78885

   N-(6-Chloro-9H-beta-carbolin-8-yl)-4-methoxy-benzamide

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: 351.79

Molecular Weight (Monoisotopic): 351.0775

AlogP: 4.58

#Rotatable Bonds: 3

Polar Surface Area: 67.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.56

CX Basic pKa: 3.50

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -1.14

References

1. Castro AC, Dang LC, Soucy F, Grenier L, Mazdiyasni H, Hottelet M, Parent L, Pien C, Palombella V, Adams J..  (2003)  Novel IKK inhibitors: beta-carbolines.,  13  (14): [PMID:12824047] [10.1016/s0960-894x(03)00408-6]

Source

Source(1):

• Scientific Literature