2-chloro-(2'-nitro)cinnamanilide

ID: ALA2251559

PubChem CID: 889827

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O3

Molecular Weight: 302.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1[N+](=O)[O-])Nc1ccccc1Cl

Standard InChI:  InChI=1S/C15H11ClN2O3/c16-12-6-2-3-7-13(12)17-15(19)10-9-11-5-1-4-8-14(11)18(20)21/h1-10H,(H,17,19)/b10-9+

Standard InChI Key:  GHQGPISGCJIZJX-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   11.9510  -11.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9499  -11.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6579  -12.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3676  -11.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3648  -11.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6561  -10.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0709  -10.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7802  -11.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4863  -10.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1962  -11.0838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4838   -9.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1996  -11.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4930  -12.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4961  -13.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2060  -13.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9144  -13.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9078  -12.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6522   -9.8663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9433   -9.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3587   -9.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7844  -11.9023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 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 12  1  0
 18 19  2  0
 18 20  1  0
  6 18  1  0
 13 21  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251559

   (E)-N-(2-chlorophenyl)-3-(2-nitrophenyl)prop-2-enamide

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: 302.72

Molecular Weight (Monoisotopic): 302.0458

AlogP: 3.90

#Rotatable Bonds: 4

Polar Surface Area: 72.24

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.98

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: -1.65

References

1. Vishnoi S, Agrawal V, Kasana VK..  (2009)  Synthesis and structure--activity relationships of substituted cinnamic acids and amide analogues: a new class of herbicides.,  57  (8): [PMID:19368353] [10.1021/jf8034385]

Source

Source(1):

• Scientific Literature