(Z)-N-(4-Amino-phenyl)-2-cyano-3-cyclopropyl-3-hydroxy-acrylamide hydrochloride

ID: ALA543919

Max Phase: Preclinical

Molecular Formula: C13H14ClN3O2

Molecular Weight: 243.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N#C/C(C(=O)Nc1ccc(N)cc1)=C(/O)C1CC1

Standard InChI:  InChI=1S/C13H13N3O2.ClH/c14-7-11(12(17)8-1-2-8)13(18)16-10-5-3-9(15)4-6-10;/h3-6,8,17H,1-2,15H2,(H,16,18);1H/b12-11-;

Standard InChI Key:  KMKJWVQYFCHGCZ-AFEZEDKISA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    9.1102   -2.8819    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -3.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347   -2.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8603   -7.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6102   -5.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  2  6  1  0
  3  7  1  0
  6  8  3  0
  5  9  1  0
  5 10  1  0
  9 10  1  0
  3 11  2  0
  7 12  1  0
  4 13  1  0
 14 15  1  0
 12 16  2  0
 12 17  1  0
 14 18  2  0
 16 18  1  0
 14 19  1  0
 17 19  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: 243.27

Molecular Weight (Monoisotopic): 243.1008

AlogP: 1.95

#Rotatable Bonds: 3

Polar Surface Area: 99.14

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.01

CX Basic pKa: 3.70

CX LogP: 0.86

CX LogD: -0.56

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.33

Np Likeness Score: -1.25

References

1. Kuo EA, Hambleton PT, Kay DP, Evans PL, Matharu SS, Little E, McDowall N, Jones CB, Hedgecock CJ, Yea CM, Chan AW, Hairsine PW, Ager IR, Tully WR, Williamson RA, Westwood R..  (1996)  Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl-3-hydroxy-N-[3'-methyl-4'-(trifluoromethyl)phenyl ] propenamide and related compounds.,  39  (23): [PMID:8917650] [10.1021/jm9604437]

Source

Source(1):

• Scientific Literature