US9162991, 19a

ID: ALA3937082

PubChem CID: 2355156

Max Phase: Preclinical

Molecular Formula: C16H13NO4

Molecular Weight: 283.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)OCc1ccccc1

Standard InChI:  InChI=1S/C16H13NO4/c18-16(21-12-14-4-2-1-3-5-14)11-8-13-6-9-15(10-7-13)17(19)20/h1-11H,12H2/b11-8+

Standard InChI Key:  BNENQSLQCVUFQE-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007    1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6971    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6919   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3903   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0939   -0.7637    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  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  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  7 20  1  0
 20 21  2  0
 21  4  1  0
M  CHG  2   1  -1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA3937082

   benzyl (E)-3-(4-nitrophenyl)prop-2-enoate

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: 283.28

Molecular Weight (Monoisotopic): 283.0845

AlogP: 3.35

#Rotatable Bonds: 5

Polar Surface Area: 69.44

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.18

CX LogD: 4.18

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.36

Np Likeness Score: -0.49

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database