8-Methoxy-4-phenylamino-quinoline-3-carboxylic acid ethyl ester hydrochloride (0.7H2o)

ID: ALA542457

PubChem CID: 20529025

Max Phase: Preclinical

Molecular Formula: C19H19ClN2O3

Molecular Weight: 322.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2c(OC)cccc2c1Nc1ccccc1.Cl

Standard InChI:  InChI=1S/C19H18N2O3.ClH/c1-3-24-19(22)15-12-20-18-14(10-7-11-16(18)23-2)17(15)21-13-8-5-4-6-9-13;/h4-12H,3H2,1-2H3,(H,20,21);1H

Standard InChI Key:  DGFFVGQOZXGJAE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  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
   -1.2964   -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
   -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 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
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7445    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
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    1.4924    0.0000 C   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
   -3.8880    3.0076    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
   -7.5506    0.8910    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
   -3.8807    6.0076    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
  4  6  1  0
  5  6  2  0
  3  7  1  0
  3  8  2  0
  5  8  1  0
  2  9  1  0
  6 10  1  0
  7 11  2  0
  9 12  1  0
  7 13  1  0
  4 14  1  0
 10 15  1  0
 14 16  2  0
 10 17  2  0
 16 17  1  0
 13 18  1  0
 12 19  2  0
 12 20  1  0
 15 21  1  0
 18 22  1  0
 20 23  2  0
 19 24  1  0
 23 25  1  0
 24 25  2  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: 322.36

Molecular Weight (Monoisotopic): 322.1317

AlogP: 4.16

#Rotatable Bonds: 5

Polar Surface Area: 60.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.06

CX LogP: 5.07

CX LogD: 5.07

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.71

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