US9162991, 4h

ID: ALA3931451

PubChem CID: 25053517

Max Phase: Preclinical

Molecular Formula: C18H13N5O5

Molecular Weight: 379.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(Cc2cccc([N+](=O)[O-])c2)nn1

Standard InChI:  InChI=1S/C18H13N5O5/c24-18(9-6-13-4-7-15(8-5-13)22(25)26)17-12-21(20-19-17)11-14-2-1-3-16(10-14)23(27)28/h1-10,12H,11H2/b9-6+

Standard InChI Key:  ALVRGEGYRAZIRZ-RMKNXTFCSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    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
   -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
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056   -3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3371   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -5.2877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -3.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110   -6.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051   -6.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5938   -7.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   -9.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521  -10.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7252  -11.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056  -13.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128  -13.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396  -11.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592  -10.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900  -14.5628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7956  -14.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869  -15.5397    0.0000 O   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  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25 26  1  0
 25 27  2  0
  8 28  2  0
 28  4  1  0
M  CHG  4   1  -1   2   1  25   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3931451

   (E)-3-(4-nitrophenyl)-1-[1-[(3-nitrophenyl)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: 379.33

Molecular Weight (Monoisotopic): 379.0917

AlogP: 3.04

#Rotatable Bonds: 7

Polar Surface Area: 134.06

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: -1.58

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database