7-[2-(4-Bromo-phenyl)-ethoxy]-4-hydroxy-quinoline-3-carboxylic acid

ID: ALA160432

PubChem CID: 44371804

Max Phase: Preclinical

Molecular Formula: C18H14BrNO4

Molecular Weight: 388.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCCc3ccc(Br)cc3)ccc2c1O

Standard InChI:  InChI=1S/C18H14BrNO4/c19-12-3-1-11(2-4-12)7-8-24-13-5-6-14-16(9-13)20-10-15(17(14)21)18(22)23/h1-6,9-10H,7-8H2,(H,20,21)(H,22,23)

Standard InChI Key:  KBCFANALXYKKFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.5417   -4.0500    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
    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
    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
   -0.4583   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -3.4875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -5.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -4.0250    0.0000 C   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
    3.1417   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -5.5875    0.0000 C   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  3  2  0
  9  4  2  0
 10  6  2  0
 11  9  1  0
 12  2  1  0
 13  6  1  0
 14  8  1  0
 15 19  2  0
 16 24  1  0
 17 15  1  0
 18 20  2  0
 19 21  1  0
 20 16  1  0
 21 16  2  0
 22 11  1  0
 23 22  1  0
 24 23  1  0
  3  4  1  0
 14 11  2  0
 18 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA160432

   7-[2-(4-bromophenyl)ethoxy]-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: 388.22

Molecular Weight (Monoisotopic): 387.0106

AlogP: 4.02

#Rotatable Bonds: 5

Polar Surface Area: 79.65

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.77

CX Basic pKa: 1.57

CX LogP: 4.76

CX LogD: 1.39

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -0.54

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