2-chloro-(3'-nitro)cinnamanilide

ID: ALA2251560

PubChem CID: 692312

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O3

Molecular Weight: 302.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc([N+](=O)[O-])c1)Nc1ccccc1Cl

Standard InChI:  InChI=1S/C15H11ClN2O3/c16-13-6-1-2-7-14(13)17-15(19)9-8-11-4-3-5-12(10-11)18(20)21/h1-10H,(H,17,19)/b9-8+

Standard InChI Key:  ASWCHXLMADGNSY-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   17.7085  -10.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7074  -11.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4154  -12.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1251  -11.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1223  -10.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4136  -10.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8284  -10.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5377  -10.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2438  -10.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9537  -10.8361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2413   -9.6130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9571  -11.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2505  -12.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2536  -12.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9635  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6719  -12.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6653  -12.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4173  -12.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1249  -13.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7095  -13.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5419  -11.6547    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
  3 18  1  0
 13 21  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251560

   (2E)-N-(2-chlorophenyl)-3-(3-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: 12.99

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: -1.61

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]

2. De Petrocellis L, Ortar G, Schiano Moriello A, Serum EM, Rusterholz DB..  (2015)  Structure-activity relationships of the prototypical TRPM8 agonist icilin.,  25  (11): [PMID:25935641] [10.1016/j.bmcl.2015.04.032]

Source

Source(1):

• Scientific Literature