9-amino-2-cyclobutyl-5-(2-methoxypyridin-3-yl)-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one

ID: ALA1783287

Max Phase: Preclinical

Molecular Formula: C21H20N4O2

Molecular Weight: 360.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ncccc1-c1cccc2c(N)c3c(nc12)CN(C1CCC1)C3=O

Standard InChI:  InChI=1S/C21H20N4O2/c1-27-20-14(9-4-10-23-20)13-7-3-8-15-18(22)17-16(24-19(13)15)11-25(21(17)26)12-5-2-6-12/h3-4,7-10,12H,2,5-6,11H2,1H3,(H2,22,24)

Standard InChI Key:  NRBRKRZMKXLHTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -3.0473   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484   -1.6648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336   -2.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172   -1.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354   -0.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4762   -0.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    2.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0598    1.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    0.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    0.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220    2.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803    0.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0638    1.2337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    2.8718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8262    2.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908    1.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4766    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0575    1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    1.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  2  0
 13 14  1  0
  1  7  1  0
 14 15  1  0
 15 18  2  0
  3  4  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
  7  8  1  0
  6  9  1  0
  9 14  2  0
  4  5  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 13 10  2  0
 16 22  1  0
  2  3  1  0
 21 23  2  0
 24 25  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
 12  9  1  0
 25 26  1  0
 26 27  1  0
 27 24  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1783287

   ---

2. Alternative Forms:

   

   ALA1783287

   9-amino-2-cyclobutyl-5-(2-(111C)methoxypyridin-3-yl)-3H-pyrrolo[3,4-b]quinolin-1-one

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: 360.42

Molecular Weight (Monoisotopic): 360.1586

AlogP: 3.40

#Rotatable Bonds: 3

Polar Surface Area: 81.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.70

CX Basic pKa: 5.38

CX LogP: 2.86

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.77

Np Likeness Score: -0.60

References

1. Alhambra C, Becker C, Blake T, Chang AH, Damewood JR, Daniels T, Dembofsky BT, Gurley DA, Hall JE, Herzog KJ, Horchler CL, Ohnmacht CJ, Schmiesing RJ, Dudley A, Ribadeneira MD, Knappenberger KS, Maciag C, Stein MM, Chopra M, Liu XF, Christian EP, Arriza JL, Chapdelaine MJ..  (2011)  Development and SAR of functionally selective allosteric modulators of GABAA receptors.,  19  (9): [PMID:21498079] [10.1016/j.bmc.2011.03.035]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data