7-Ethyl-3-hydroxyquinolin-2(1H)-one

ID: ALA445463

PubChem CID: 44157568

Max Phase: Preclinical

Molecular Formula: C11H11NO2

Molecular Weight: 189.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc2cc(O)c(=O)[nH]c2c1

Standard InChI:  InChI=1S/C11H11NO2/c1-2-7-3-4-8-6-10(13)11(14)12-9(8)5-7/h3-6,13H,2H2,1H3,(H,12,14)

Standard InChI Key:  AOGSDHLADKKXMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   14.1153  -11.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1141  -12.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8285  -12.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8267  -11.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5417  -11.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5405  -12.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2569  -12.7622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9792  -12.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9804  -11.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2593  -11.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6954  -11.1061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6921  -12.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3997  -12.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3991  -13.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  0
  4  1  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  5  6  1  0
  9 11  1  0
  8 12  2  0
  2  3  1  0
  2 13  1  0
  3  6  2  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA445463

   3-hydroxyquinolin-2(1H)-one, 16

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: 189.21

Molecular Weight (Monoisotopic): 189.0790

AlogP: 1.80

#Rotatable Bonds: 1

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.07

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 1.81

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.72

Np Likeness Score: -0.25

References

1. Duplantier AJ, Becker SL, Bohanon MJ, Borzilleri KA, Chrunyk BA, Downs JT, Hu LY, El-Kattan A, James LC, Liu S, Lu J, Maklad N, Mansour MN, Mente S, Piotrowski MA, Sakya SM, Sheehan S, Steyn SJ, Strick CA, Williams VA, Zhang L..  (2009)  Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors.,  52  (11): [PMID:19438227] [10.1021/jm900128w]

Source

Source(1):

• Scientific Literature