4-Hydroxy-7-pentachlorophenylmethoxy-quinoline-3-carboxylic acid

ID: ALA156108

PubChem CID: 44371905

Max Phase: Preclinical

Molecular Formula: C17H8Cl5NO4

Molecular Weight: 467.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCc3c(Cl)c(Cl)c(Cl)c(Cl)c3Cl)ccc2c1O

Standard InChI:  InChI=1S/C17H8Cl5NO4/c18-11-9(12(19)14(21)15(22)13(11)20)5-27-6-1-2-7-10(3-6)23-4-8(16(7)24)17(25)26/h1-4H,5H2,(H,23,24)(H,25,26)

Standard InChI Key:  UHFJYZJYSZTRNV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.2375   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -6.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -5.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -2.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -7.1375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -8.1875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4625   -5.0542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -5.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -4.0167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -7.1417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -2.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500   -4.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  8  2  0
  4  6  1  0
  5  7  2  0
  6  1  2  0
  7  1  1  0
  8  9  1  0
  9 15  2  0
 10 16  2  0
 11 10  1  0
 12  3  1  0
 13 11  2  0
 14  1  1  0
 15 27  1  0
 16 24  1  0
 17 12  2  0
 18  2  1  0
 19  5  1  0
 20  4  1  0
 21 14  1  0
 22  6  1  0
 23  7  1  0
 24 21  1  0
 25  8  1  0
 26 12  1  0
 27 24  2  0
  4  2  2  0
  9 10  1  0
  3 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA156108

   4-oxo-7-[(2,3,4,5,6-pentachlorophenyl)methoxy]-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: 467.52

Molecular Weight (Monoisotopic): 464.8896

AlogP: 6.48

#Rotatable Bonds: 4

Polar Surface Area: 79.65

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.76

CX Basic pKa: 1.56

CX LogP: 6.72

CX LogD: 3.35

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.34

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]

Source

Source(1):

• Scientific Literature