4-Hydroxy-quinoline-3,7-dicarboxylic acid

ID: ALA139078

Chembl Id: CHEMBL139078

Cas Number: 63463-25-2

PubChem CID: 328523

Max Phase: Preclinical

Molecular Formula: C11H7NO5

Molecular Weight: 233.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H7NO5/c13-9-6-2-1-5(10(14)15)3-8(6)12-4-7(9)11(16)17/h1-4H,(H,12,13)(H,14,15)(H,16,17)

Standard InChI Key:  QLHSVJRXHWXBHT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA139078

   4-oxo-1H-quinoline-3,7-dicarboxylic 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: 233.18

Molecular Weight (Monoisotopic): 233.0324

AlogP: 1.34

#Rotatable Bonds: 2

Polar Surface Area: 107.72

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: 0.04

CX LogP: 1.79

CX LogD: -4.94

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.72

Np Likeness Score: -0.44

References

1. Dove S, Coats E, Scharfenberg P, Franke R..  (1985)  7-substituted-4-hydroxyquinoline-3-carboxylic acids as inhibitors of dehydrogenase enzymes and of the respiration of Ehrlich ascites tumor cells: multivariate analysis and quantitative structure-activity relationship for polar substituents.,  28  (4): [PMID:3981536] [10.1021/jm00382a010]

2. 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]

3. Golub AG, Yakovenko OY, Bdzhola VG, Sapelkin VM, Zien P, Yarmoluk SM..  (2006)  Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2.,  49  (22): [PMID:17064064] [10.1021/jm050048t]

4. 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