US9162991, 4b

ID: ALA3890724

PubChem CID: 25053513

Max Phase: Preclinical

Molecular Formula: C19H24N4O3

Molecular Weight: 356.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCn1cc(C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)nn1

Standard InChI:  InChI=1S/C19H24N4O3/c1-2-3-4-5-6-7-14-22-15-18(20-21-22)19(24)13-10-16-8-11-17(12-9-16)23(25)26/h8-13,15H,2-7,14H2,1H3/b13-10+

Standard InChI Key:  FGRMZTDGVYGEEX-JLHYYAGUSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.7884  -17.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818  -16.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064  -15.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0236  -13.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1482  -12.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654  -11.3509    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
    5.5071   -8.7638    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
    5.1017   -6.1218    0.0000 C   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
    2.6747   -6.1134    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
    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
    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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  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
 21 24  1  0
 24 25  1  0
 24 26  2  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3890724

   (E)-3-(4-nitrophenyl)-1-(1-octyltriazol-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: 356.43

Molecular Weight (Monoisotopic): 356.1848

AlogP: 4.44

#Rotatable Bonds: 11

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: 5.37

CX LogD: 5.37

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.20

Np Likeness Score: -1.20

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database