7-Carbamoyl-4-hydroxy-quinoline-3-carboxylic acid

ID: ALA160456

Cas Number: 63463-24-1

PubChem CID: 328522

Max Phase: Preclinical

Molecular Formula: C11H8N2O4

Molecular Weight: 232.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc2c(O)c(C(=O)O)cnc2c1

Standard InChI:  InChI=1S/C11H8N2O4/c12-10(15)5-1-2-6-8(3-5)13-4-7(9(6)14)11(16)17/h1-4H,(H2,12,15)(H,13,14)(H,16,17)

Standard InChI Key:  QKDFNNISCQNAOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    3.6125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -5.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -6.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -5.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -3.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  1  0
  5  7  2  0
  6  1  1  0
  7  1  1  0
  8  9  1  0
  9 10  1  0
 10  4  2  0
 11  3  2  0
 12 11  1  0
 13  6  2  0
 14  8  2  0
 15  8  1  0
 16  2  1  0
 17  6  1  0
  3  4  1  0
 12  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA160456

   7-carbamoyl-4-oxo-1H-quinoline-3-carboxylic acid

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: 232.19

Molecular Weight (Monoisotopic): 232.0484

AlogP: 0.74

#Rotatable Bonds: 2

Polar Surface Area: 113.51

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: 0.55

CX LogP: 0.99

CX LogD: -2.40

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.71

Np Likeness Score: -0.73

References

1. Coats EA, Shah KJ, Milstein SR, Genther CS, Nene DM, Roesener J, Schmidt J, Pleiss M, Wagner E, Baker JK..  (1982)  4-hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions.,  25  (1): [PMID:7086823] [10.1021/jm00343a011]

2. Shah KJ, Coats EA..  (1977)  Design, synthesis, and correlation analysis of 7-substituted 4-hydroxyquinoline-3-carboxylic acids as inhibitors of cellular respiration.,  20  (8): [PMID:894670] [10.1021/jm00218a003]

Source

Source(1):

• Scientific Literature