4-nitro-(3'-chloro)cinnamanilide

ID: ALA2251544

PubChem CID: 5736987

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O3

Molecular Weight: 302.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(Cl)c1)Nc1ccc([N+](=O)[O-])cc1

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

Standard InChI Key:  BPKFRLNHVIQVII-RUDMXATFSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   29.0832  -15.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0820  -16.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7901  -16.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4997  -16.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4969  -15.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7883  -14.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2031  -14.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9123  -15.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6185  -14.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3283  -15.2192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6160  -13.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3317  -16.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6252  -16.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6282  -17.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3382  -17.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0465  -17.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0399  -16.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7899  -17.2793    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.3438  -18.4896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0537  -18.8943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6383  -18.9021    0.0000 O   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
  3 18  1  0
 19 20  2  0
 19 21  1  0
 15 19  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251544

   4-NITRO-(3'-CHLORO)CINNAMANILIDE

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: 13.34

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: -1.54

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