US9162991, 4c

ID: ALA3920367

PubChem CID: 25053514

Max Phase: Preclinical

Molecular Formula: C16H16N4O3

Molecular Weight: 312.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cn(C2CCCC2)nn1

Standard InChI:  InChI=1S/C16H16N4O3/c21-16(10-7-12-5-8-14(9-6-12)20(22)23)15-11-19(18-17-15)13-3-1-2-4-13/h5-11,13H,1-4H2/b10-7+

Standard InChI Key:  QRNSFLCNPQFNES-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 23 25  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
    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
    5.5111   -8.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9900   -8.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3355  -10.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540  -11.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9165  -10.1283    0.0000 C   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  2  0
 18 14  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  CHG  2  11   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3920367

   (E)-1-(1-cyclopentyltriazol-4-yl)-3-(4-nitrophenyl)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: 312.33

Molecular Weight (Monoisotopic): 312.1222

AlogP: 3.20

#Rotatable Bonds: 5

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: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.37

Np Likeness Score: -1.33

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database