4-Hydroxy-quinoline-3-carboxylic acid

ID: ALA158890

Cas Number: 13721-01-2

PubChem CID: 220875

Product Number: D155342, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H7NO3

Molecular Weight: 189.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2ccccc2c1O

Standard InChI:  InChI=1S/C10H7NO3/c12-9-6-3-1-2-4-8(6)11-5-7(9)10(13)14/h1-5H,(H,11,12)(H,13,14)

Standard InChI Key:  ILNJBIQQAIIMEY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   -4.1514    1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1526    0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4378   -0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4396    1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    1.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7234    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0081   -0.2175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931    0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979    1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0138    1.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0181    2.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5859    1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1310    1.0360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909    2.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  1  2  2  0
  7  8  2  0
  5  4  2  0
  8  9  1  0
  4  1  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
  2  3  1  0
  9 12  1  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 12 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA158890

   1,4-Dihydro-4-oxoquinoline-3-carboxylic Acid

Molecule Features

Natural Product: Yes

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: 189.17

Molecular Weight (Monoisotopic): 189.0426

AlogP: 1.64

#Rotatable Bonds: 1

Polar Surface Area: 70.42

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.68

CX Basic pKa: 1.46

CX LogP: 2.13

CX LogD: -1.24

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.71

Np Likeness Score: -0.47

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. 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]

3. Li GX, Liu ZQ, Luo XY..  (2010)  Dichloro-4-quinolinol-3-carboxylic acid: synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA.,  45  (5): [PMID:20122762] [10.1016/j.ejmech.2010.01.018]

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]

5. Helgren TR, Seven ES, Chen C, Edwards TE, Staker BL, Abendroth J, Myler PJ, Horn JR, Hagen TJ..  (2018)  The identification of inhibitory compounds of Rickettsia prowazekii methionine aminopeptidase for antibacterial applications.,  28  (8): [PMID:29551481] [10.1016/j.bmcl.2018.03.002]

6. Mori S, Iinuma H, Manaka N, Ishigami-Yuasa M, Murayama T, Nishijima Y, Sakurai A, Arai R, Kurebayashi N, Sakurai T, Kagechika H..  (2019)  Structural development of a type-1 ryanodine receptor (RyR1) Ca²⁺-release channel inhibitor guided by endoplasmic reticulum Ca²⁺ assay.,  179  [PMID:31299492] [10.1016/j.ejmech.2019.06.076]

7. Zhang H, Daněk O, Makarov D, Rádl S, Kim D, Ledvinka J, Vychodilová K, Hlaváč J, Lefèbre J, Denis M, Rademacher C, Ménová P..  (2022)  Drug-like Inhibitors of DC-SIGN Based on a Quinolone Scaffold.,  13  (6.0): [PMID:35707152] [10.1021/acsmedchemlett.2c00067]

Source

Source(1):

• Scientific Literature