2-Cyano-3-hydroxy-3,N-bis-(4-trifluoromethyl-phenyl)-acrylamide

ID: ALA432994

Chembl Id: CHEMBL432994

Max Phase: Preclinical

Molecular Formula: C18H10F6N2O2

Molecular Weight: 400.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(C(=O)Nc1ccc(C(F)(F)F)cc1)=C(/O)c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C18H10F6N2O2/c19-17(20,21)11-3-1-10(2-4-11)15(27)14(9-25)16(28)26-13-7-5-12(6-8-13)18(22,23)24/h1-8,27H,(H,26,28)/b15-14-

Standard InChI Key:  QCILWKSVVYMKMI-PFONDFGASA-N

Alternative Forms

1. Parent:

   

   ALA432994

   ---

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: 400.28

Molecular Weight (Monoisotopic): 400.0646

AlogP: 5.16

#Rotatable Bonds: 3

Polar Surface Area: 73.12

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.61

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 2.63

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: -1.30

References

1. Sjogren EB, Rider MA, Nelson PH, Bingham S, Poulton AL, Emanuel MA, Komuniecki R..  (1991)  Synthesis and biological activity of a series of diaryl-substituted alpha-cyano-beta-hydroxypropenamides, a new class of anthelmintic agents.,  34  (11): [PMID:1956049] [10.1021/jm00115a020]

2. 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