4-Hydroxy-7-[2-(4-phenoxy-phenyl)-ethoxy]-quinoline-3-carboxylic acid

ID: ALA348630

PubChem CID: 44371793

Max Phase: Preclinical

Molecular Formula: C24H19NO5

Molecular Weight: 401.42

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2cc(OCCc3ccc(Oc4ccccc4)cc3)ccc2c1O

Standard InChI:  InChI=1S/C24H19NO5/c26-23-20-11-10-19(14-22(20)25-15-21(23)24(27)28)29-13-12-16-6-8-18(9-7-16)30-17-4-2-1-3-5-17/h1-11,14-15H,12-13H2,(H,25,26)(H,27,28)

Standard InChI Key:  SPDHJJIYQNRXGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  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
   -1.3583   -3.4792    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
   -0.4583   -4.0042    0.0000 C   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
   -1.3500   -2.4417    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
    0.4500   -3.4917    0.0000 C   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
    1.3500   -4.0250    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
    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
   -0.4458   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.3625    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 14  1  0
 12  9  1  0
 13  2  1  0
 14 20  1  0
 15  6  1  0
 16  8  1  0
 17 11  1  0
 18 25  1  0
 19 21  1  0
 20 22  2  0
 21 18  2  0
 22 18  1  0
 23 12  1  0
 24 23  1  0
 25 24  1  0
 26 17  2  0
 27 17  1  0
 28 27  2  0
 29 26  1  0
 30 28  1  0
  3  4  1  0
 16 12  2  0
 19 14  2  0
 29 30  2  0
M  END

Associated Targets(non-human)

MDH2 Malate dehydrogenase mitochondrial (131 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDH1 Malate dehydrogenase cytoplasmic (54 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ehrlich (1318 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 401.42Molecular Weight (Monoisotopic): 401.1263AlogP: 5.05#Rotatable Bonds: 7
Polar Surface Area: 88.88Molecular Species: ACIDHBA: 5HBD: 2
#RO5 Violations: 1HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.77CX Basic pKa: 1.57CX LogP: 5.49CX LogD: 2.12
Aromatic Rings: 4Heavy Atoms: 30QED Weighted: 0.45Np Likeness Score: -0.44

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