US9162991, 4e

ID: ALA3936932

PubChem CID: 25053515

Max Phase: Preclinical

Molecular Formula: C17H13N5O3

Molecular Weight: 335.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(Cc2ccccn2)nn1

Standard InChI:  InChI=1S/C17H13N5O3/c23-17(9-6-13-4-7-15(8-5-13)22(24)25)16-12-21(20-19-16)11-14-3-1-2-10-18-14/h1-10,12H,11H2/b9-6+

Standard InChI Key:  YPPYWURDJUINLB-RMKNXTFCSA-N

Molfile:  

     RDKit          2D

 25 27  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
    5.7631  -11.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1435  -12.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507  -12.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774  -11.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971  -10.2783    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 23  2  0
 23 18  1  0
 16 24  1  0
 24 25  2  0
 25 14  1  0
M  CHG  2  11   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3936932

   (E)-3-(4-nitrophenyl)-1-[1-(pyridin-2-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: 335.32

Molecular Weight (Monoisotopic): 335.1018

AlogP: 2.53

#Rotatable Bonds: 6

Polar Surface Area: 103.81

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.54

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.30

Np Likeness Score: -1.85

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database