US9162991, 4m

ID: ALA3974183

PubChem CID: 25053576

Max Phase: Preclinical

Molecular Formula: C14H11N7O3

Molecular Weight: 325.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(Cc2cnn[nH]2)nn1

Standard InChI:  InChI=1S/C14H11N7O3/c22-14(6-3-10-1-4-12(5-2-10)21(23)24)13-9-20(19-17-13)8-11-7-15-18-16-11/h1-7,9H,8H2,(H,15,16,18)/b6-3+

Standard InChI Key:  AFQOAZMIYXNWBX-ZZXKWVIFSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.9336   -3.1588    0.0000 O   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
    2.5973   -1.5031    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
    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
   -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
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   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
    5.1017   -6.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332   -7.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5071   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900  -10.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399  -11.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285  -12.5239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624  -11.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296  -10.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 16 23  1  0
 23 24  2  0
 24 14  1  0
M  CHG  2  11   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3974183

   (E)-3-(4-nitrophenyl)-1-[1-(2H-triazol-4-ylmethyl)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: 325.29

Molecular Weight (Monoisotopic): 325.0923

AlogP: 1.25

#Rotatable Bonds: 6

Polar Surface Area: 132.49

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.66

CX Basic pKa: 0.81

CX LogP: 1.83

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.31

Np Likeness Score: -1.61

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database