US9162991, 27a

ID: ALA3951061

PubChem CID: 876507

Max Phase: Preclinical

Molecular Formula: C17H16N2O3

Molecular Weight: 296.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1ccccc1)C(=O)/C=C/c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C17H16N2O3/c1-18(13-15-5-3-2-4-6-15)17(20)12-9-14-7-10-16(11-8-14)19(21)22/h2-12H,13H2,1H3/b12-9+

Standard InChI Key:  VDESPOCMEYSKBK-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    1.5548   -3.6021    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
    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
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    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
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -8.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -9.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769  -10.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -9.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -8.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1686  -12.0126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264  -12.6075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2047  -12.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3951061

   (E)-N-benzyl-N-methyl-3-(4-nitrophenyl)prop-2-enamide

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: 296.33

Molecular Weight (Monoisotopic): 296.1161

AlogP: 3.27

#Rotatable Bonds: 5

Polar Surface Area: 63.45

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.48

Np Likeness Score: -1.20

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database