US9162991, 26a

ID: ALA3961439

PubChem CID: 102474389

Max Phase: Preclinical

Molecular Formula: C21H16N2O3

Molecular Weight: 344.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)N1Cc2cccc3cccc(c23)C1

Standard InChI:  InChI=1S/C21H16N2O3/c24-20(12-9-15-7-10-19(11-8-15)23(25)26)22-13-17-5-1-3-16-4-2-6-18(14-22)21(16)17/h1-12H,13-14H2/b12-9+

Standard InChI Key:  YKYSZHUIZHXCHD-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.9086  -10.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725   -9.7587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304  -10.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824   -7.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876   -6.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   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
    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
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    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
    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
    2.5895   -6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844   -7.5034    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 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 12  1  0
 22 24  2  0
 24 14  1  0
 24 18  1  0
  7 25  1  0
 25 26  2  0
 26  4  1  0
M  CHG  2   1  -1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA3961439

   (E)-1-(1,3-dihydrobenzo[de]isoquinolin-2-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: 344.37

Molecular Weight (Monoisotopic): 344.1161

AlogP: 4.30

#Rotatable Bonds: 3

Polar Surface Area: 63.45

Molecular Species: NEUTRAL

HBA: 3

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: 3

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -0.60

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database