US9162991, 4n

ID: ALA3889690

PubChem CID: 25053577

Max Phase: Preclinical

Molecular Formula: C19H16N4O4

Molecular Weight: 364.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2cc(C(=O)/C=C/c3ccc([N+](=O)[O-])cc3)nn2)cc1

Standard InChI:  InChI=1S/C19H16N4O4/c1-27-17-9-4-15(5-10-17)12-22-13-18(20-21-22)19(24)11-6-14-2-7-16(8-3-14)23(25)26/h2-11,13H,12H2,1H3/b11-6+

Standard InChI Key:  XQUIQFOPFXYYED-IZZDOVSWSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -1.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7433    0.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2371    1.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6194   -0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1129   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9891   -1.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4819   -1.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3552   -2.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7355   -4.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2427   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3695   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6067   -5.5580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1095   -6.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8012   -5.4430    0.0000 O   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  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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
  6 26  1  0
 26 27  2  0
 27  3  1  0
M  CHG  2  23   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3889690

   (E)-1-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-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: 364.36

Molecular Weight (Monoisotopic): 364.1172

AlogP: 3.14

#Rotatable Bonds: 7

Polar Surface Area: 100.15

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -1.38

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database