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

ID: ALA1631466

Max Phase: Preclinical

Molecular Formula: C19H17N5O

Molecular Weight: 331.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c2c(nc3c(-c4ncccn4)cccc13)CN(C1CCC1)C2=O

Standard InChI:  InChI=1S/C19H17N5O/c20-16-12-6-2-7-13(18-21-8-3-9-22-18)17(12)23-14-10-24(11-4-1-5-11)19(25)15(14)16/h2-3,6-9,11H,1,4-5,10H2,(H2,20,23)

Standard InChI Key:  TWSTVDPXWQPIIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   19.4694    2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4682    1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1831    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1813    2.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8966    2.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8974    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6127    0.7700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6071    2.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1858   -0.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4706   -0.4706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4722   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1882   -1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9040   -1.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8990   -0.4650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6027    3.2470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3230    2.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3261    1.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1135    0.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5971    1.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1085    2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3604    3.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4218    1.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0074    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5885    1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0029    2.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  3  9  1  0
  6  7  1  0
  8 15  1  0
 16 17  1  0
  7 17  2  0
  1  2  2  0
 16  8  2  0
  8  5  1  0
  5  4  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  4  1  1  0
 20 21  2  0
 22 23  1  0
  9 10  2  0
 10 11  1  0
  2  3  1  0
 23 24  1  0
 24 25  1  0
 25 22  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1631466

   ---

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: 331.38

Molecular Weight (Monoisotopic): 331.1433

AlogP: 2.78

#Rotatable Bonds: 2

Polar Surface Area: 85.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.66

CX Basic pKa: 4.88

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.67

References

1. Liu XF, Chang HF, Schmiesing RJ, Wesolowski SS, Knappenberger KS, Arriza JL, Chapdelaine MJ..  (2010)  Developing dual functional allosteric modulators of GABA(A) receptors.,  18  (23): [PMID:20980155] [10.1016/j.bmc.2010.09.058]

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