US9162991, 4j

ID: ALA3957901

PubChem CID: 25053573

Max Phase: Preclinical

Molecular Formula: C20H12F6N4O3

Molecular Weight: 470.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)nn1

Standard InChI:  InChI=1S/C20H12F6N4O3/c21-19(22,23)14-7-13(8-15(9-14)20(24,25)26)10-29-11-17(27-28-29)18(31)6-3-12-1-4-16(5-2-12)30(32)33/h1-9,11H,10H2/b6-3+

Standard InChI Key:  WBOLHGCBRRPKFO-ZZXKWVIFSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    0.0000 F   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
    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
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    5.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    5.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    4.2349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532    3.1236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5322    6.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320    7.8763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0256    7.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437    8.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1370    8.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7567    9.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2496   10.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1228    8.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5032    7.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0103    7.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6168    9.0047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3139    8.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1144   10.0967    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
   -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
   -2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -2.1009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 24 26  2  0
  7 27  2  0
 27 28  1  0
 28 29  2  0
 29  5  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3957901

   (E)-1-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]triazol-4-yl]-3-(4-nitrophenyl)prop-2-en-1-one

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: 470.33

Molecular Weight (Monoisotopic): 470.0814

AlogP: 5.17

#Rotatable Bonds: 6

Polar Surface Area: 90.92

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.74

CX LogD: 5.74

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -1.43

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database