US9162991, 16a

ID: ALA3977914

PubChem CID: 25023627

Max Phase: Preclinical

Molecular Formula: C14H9N5O4

Molecular Weight: 311.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)[n+]1nn([O-])c2ncccc21

Standard InChI:  InChI=1S/C14H9N5O4/c20-13(8-5-10-3-6-11(7-4-10)19(22)23)17-12-2-1-9-15-14(12)18(21)16-17/h1-9H/b8-5+

Standard InChI Key:  VVHQTMAVBQRNPP-VMPITWQZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -0.1507  -13.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478  -12.3277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227  -12.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764  -10.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918  -10.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -9.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -8.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -6.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631   -3.8341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5871   -1.5034    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 N   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
    0.7083   -8.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -9.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  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 12  1  0
 21 16  1  0
  7 22  1  0
 22 23  2  0
 23  4  1  0
M  CHG  4   1  -1   2   1  12   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3977914

   (E)-3-(4-nitrophenyl)-1-(3-oxidotriazolo[4,5-b]pyridin-3-ium-1-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: 311.26

Molecular Weight (Monoisotopic): 311.0655

AlogP: 1.33

#Rotatable Bonds: 3

Polar Surface Area: 117.86

Molecular Species: ACID

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.16

CX Basic pKa: ┄

CX LogP: -1.02

CX LogD: -2.19

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.31

Np Likeness Score: -0.73

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database