8-Methoxy-4-o-tolylamino-quinoline-3-carboxylic acid hydrochloride

ID: ALA553136

PubChem CID: 45261602

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O3

Molecular Weight: 308.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c(Nc3ccccc3C)c(C(=O)O)cnc12.Cl

Standard InChI:  InChI=1S/C18H16N2O3.ClH/c1-11-6-3-4-8-14(11)20-16-12-7-5-9-15(23-2)17(12)19-10-13(16)18(21)22;/h3-10H,1-2H3,(H,19,20)(H,21,22);1H

Standard InChI Key:  CSFTWNYYKHEIRE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    5.1003    1.1305    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506    0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138    2.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    5.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    6.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -3.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852    3.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    5.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  4  7  1  0
  6  7  2  0
  3  8  1  0
  3  9  2  0
  6  9  1  0
  5 10  1  0
  7 11  1  0
  8 12  2  0
 10 13  2  0
  8 14  1  0
  4 15  1  0
 11 16  1  0
 15 17  2  0
 10 18  1  0
 11 19  2  0
 17 19  1  0
 13 20  1  0
 13 21  1  0
 16 22  1  0
 18 23  2  0
 21 24  2  0
 23 24  1  0
M  END

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: 308.34

Molecular Weight (Monoisotopic): 308.1161

AlogP: 3.99

#Rotatable Bonds: 4

Polar Surface Area: 71.45

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.21

CX Basic pKa: 5.62

CX LogP: 3.48

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -1.08

References

1. Ife RJ, Brown TH, Keeling DJ, Leach CA, Meeson ML, Parsons ME, Reavill DR, Theobald CJ, Wiggall KJ..  (1992)  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-substituted-4-(phenylamino)quinolines.,  35  (18): [PMID:1326634] [10.1021/jm00096a018]

Source

Source(1):

• Scientific Literature