2-(2,4-Dihydroxy-benzylcarbamoyl)-8-hydroxy-quinoline-7-carboxylic acid

ID: ALA81714

PubChem CID: 491467

Max Phase: Preclinical

Molecular Formula: C18H14N2O6

Molecular Weight: 354.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(O)cc1O)c1ccc2ccc(C(=O)O)c(O)c2n1

Standard InChI:  InChI=1S/C18H14N2O6/c21-11-4-1-10(14(22)7-11)8-19-17(24)13-6-3-9-2-5-12(18(25)26)16(23)15(9)20-13/h1-7,21-23H,8H2,(H,19,24)(H,25,26)

Standard InChI Key:  XCUIQBHAIMNBMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.7971   -4.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031   -4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7613   -2.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -3.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753   -4.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6428   -3.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -4.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9292   -4.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -2.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149   -4.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997   -4.4879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847   -4.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7894   -3.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687   -4.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0667   -4.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -5.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9273   -5.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6441   -4.0677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -5.3079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601   -4.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291   -2.8416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905   -2.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
  8  9  1  0
  9 12  2  0
  4  5  1  0
 18 19  1  0
 18 20  2  0
  8 18  1  0
 11 10  2  0
  9 21  1  0
 10  7  1  0
 17 22  1  0
  2  3  1  0
 17 23  2  0
  5  6  2  0
 22 24  1  0
 24  6  1  0
 11 12  1  0
  5 25  1  0
  6  1  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA81714

   2-(2,4-Dihydroxybenzylcarbamoyl)-8-hydroxyquinoline-7-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: 354.32

Molecular Weight (Monoisotopic): 354.0852

AlogP: 1.98

#Rotatable Bonds: 4

Polar Surface Area: 139.98

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.36

CX Basic pKa: 0.02

CX LogP: 2.71

CX LogD: -0.71

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: -0.31

References

1. Bénard C, Zouhiri F, Normand-Bayle M, Danet M, Desmaële D, Leh H, Mouscadet JF, Mbemba G, Thomas CM, Bonnenfant S, Le Bret M, d'Angelo J..  (2004)  Linker-modified quinoline derivatives targeting HIV-1 integrase: synthesis and biological activity.,  14  (10): [PMID:15109635] [10.1016/j.bmcl.2004.03.005]

2. Sliman F, Blairvacq M, Durieu E, Meijer L, Rodrigo J, Desmaële D..  (2010)  Identification and structure-activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase.,  20  (9): [PMID:20363627] [10.1016/j.bmcl.2010.03.061]

Source

Source(1):

• Scientific Literature