(Z)-2-Cyano-3-cyclobutyl-3-hydroxy-N-(4-trifluoromethyl-phenyl)-acrylamide

ID: ALA337130

Max Phase: Preclinical

Molecular Formula: C15H13F3N2O2

Molecular Weight: 310.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(C(=O)Nc1ccc(C(F)(F)F)cc1)=C(/O)C1CCC1

Standard InChI:  InChI=1S/C15H13F3N2O2/c16-15(17,18)10-4-6-11(7-5-10)20-14(22)12(8-19)13(21)9-2-1-3-9/h4-7,9,21H,1-3H2,(H,20,22)/b13-12-

Standard InChI Key:  KHCOEDQDAYSFBQ-SEYXRHQNSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   11.3167  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8000  -10.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8417  -10.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792  -10.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3167  -11.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2792  -10.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3167  -11.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7917   -9.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2667  -10.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792  -10.2167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750  -11.2625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292  -10.1542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792  -11.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792  -10.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6750  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8417   -9.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750  -11.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750  -10.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8667  -11.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8667  -10.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2625  -11.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  8  1  0
  5  1  1  0
  6  2  1  0
  7  5  3  0
  8 15  1  0
  9  2  2  0
 10  3  1  0
 11  4  1  0
 12  4  1  0
 13  4  1  0
 14 18  1  0
 15 19  2  0
 16  6  1  0
 17  3  1  0
 18 16  2  0
 19 16  1  0
 20 22  1  0
 21 10  1  0
 22 10  1  0
 20 21  1  0
  8 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA337130

   ---

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: 310.28

Molecular Weight (Monoisotopic): 310.0929

AlogP: 3.78

#Rotatable Bonds: 3

Polar Surface Area: 73.12

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.25

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 0.87

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: -1.48

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]

2. Kuo PY, Shie TL, Chen YS, Lai JT, Yang DY..  (2006)  Enzyme inhibition potency enhancement by active site metal chelating and hydrogen bonding induced conformation-restricted cyclopropanecarbonyl derivatives.,  16  (23): [PMID:16979340] [10.1016/j.bmcl.2006.08.125]

Source

Source(1):

• Scientific Literature