US9162991, 4i

ID: ALA3958950

PubChem CID: 25053572

Max Phase: Preclinical

Molecular Formula: C18H9F5N4O3

Molecular Weight: 424.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(Cc2c(F)c(F)c(F)c(F)c2F)nn1

Standard InChI:  InChI=1S/C18H9F5N4O3/c19-14-11(15(20)17(22)18(23)16(14)21)7-26-8-12(24-25-26)13(28)6-3-9-1-4-10(5-2-9)27(29)30/h1-6,8H,7H2/b6-3+

Standard InChI Key:  SQAGYNCQYWDUNQ-ZZXKWVIFSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    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
    2.3383    1.3500    0.0000 F   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    2.7000    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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -1.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7433    0.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2371    1.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6194   -0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1129   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9891   -1.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4819   -1.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3552   -2.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7355   -4.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2427   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3695   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6067   -5.5580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1095   -6.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8012   -5.4430    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 F   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   -2.7000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  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  1  0
 27 28  1  0
 27 29  2  0
 29  2  1  0
 29 30  1  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3958950

   (E)-3-(4-nitrophenyl)-1-[1-[(2,3,4,5,6-pentafluorophenyl)methyl]triazol-4-yl]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: 424.29

Molecular Weight (Monoisotopic): 424.0595

AlogP: 3.83

#Rotatable Bonds: 6

Polar Surface Area: 90.92

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.70

CX LogD: 4.70

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.11

Np Likeness Score: -1.27

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database