US9162991, 14l

ID: ALA3980243

PubChem CID: 25023507

Max Phase: Preclinical

Molecular Formula: C15H10ClN3O2

Molecular Weight: 299.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(Cl)c1)[n+]1nn([O-])c2ccccc21

Standard InChI:  InChI=1S/C15H10ClN3O2/c16-12-5-3-4-11(10-12)8-9-15(20)18-13-6-1-2-7-14(13)19(21)17-18/h1-10H/b9-8+

Standard InChI Key:  AOFZAIKOPGVTOF-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -0.4916   -3.8582    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
    3.8794   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -0.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823   -2.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3509   -2.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -3.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8221   -3.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8221   -4.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -5.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8857   -5.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5111   -7.0512    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8856   -4.7932    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
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15  9  1  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 21 16  1  0
M  CHG  2   1  -1   4   1
M  END

Alternative Forms

1. Parent:

   

   ALA3980243

   (E)-3-(3-chlorophenyl)-1-(3-oxidobenzotriazol-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: 299.72

Molecular Weight (Monoisotopic): 299.0462

AlogP: 2.68

#Rotatable Bonds: 2

Polar Surface Area: 61.83

Molecular Species: ACID

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.80

CX Basic pKa: ┄

CX LogP: 0.50

CX LogD: -0.55

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.54

Np Likeness Score: -0.54

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database