US9162991, 4k

ID: ALA3961578

PubChem CID: 25053574

Max Phase: Preclinical

Molecular Formula: C19H16N4O3

Molecular Weight: 348.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(c1ccccc1)n1cc(C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)nn1

Standard InChI:  InChI=1S/C19H16N4O3/c1-14(16-5-3-2-4-6-16)22-13-18(20-21-22)19(24)12-9-15-7-10-17(11-8-15)23(25)26/h2-14H,1H3/b12-9+

Standard InChI Key:  VKTNCUUHHUSGOY-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    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
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -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
    4.2111   -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
    3.5939   -7.8779    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
    4.7253  -11.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057  -13.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128  -13.1972    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
    1.9901  -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
  1  2  1  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  3  1  0
  2  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:

   

   ALA3961578

   (E)-3-(4-nitrophenyl)-1-[1-(1-phenylethyl)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: 348.36

Molecular Weight (Monoisotopic): 348.1222

AlogP: 3.69

#Rotatable Bonds: 6

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: 4.40

CX LogD: 4.40

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.29

Np Likeness Score: -1.03

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database