US9162991, 28a

ID: ALA3927354

Cas Number: 140399-53-7

PubChem CID: 5828655

Max Phase: Preclinical

Molecular Formula: C18H11NO5

Molecular Weight: 321.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1cc2ccccc2oc1=O

Standard InChI:  InChI=1S/C18H11NO5/c20-16(10-7-12-5-8-14(9-6-12)19(22)23)15-11-13-3-1-2-4-17(13)24-18(15)21/h1-11H/b10-7+

Standard InChI Key:  QFXNRCNXTVYFLC-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.4299    0.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3875    1.5257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3817    2.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0919    0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0971   -0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8007   -1.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    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
    3.8990   -0.7455    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
    2.6024   -2.6977    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
    0.0000    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    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 O   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
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    0.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7903    1.5136    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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
 20 21  1  0
 21 12  1  0
 21 22  2  0
  7 23  1  0
 23 24  2  0
 24  4  1  0
M  CHG  2   1  -1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA3927354

   (E)-3-(3-(4-nitrophenyl)acryloyl)-2H-chromen-2-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: 321.29

Molecular Weight (Monoisotopic): 321.0637

AlogP: 3.60

#Rotatable Bonds: 4

Polar Surface Area: 90.42

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.24

Np Likeness Score: -0.49

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database