2-chloro-(4'-nitro)cinnamanilide

ID: ALA2251561

PubChem CID: 790360

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O3

Molecular Weight: 302.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)Nc1ccccc1Cl

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

Standard InChI Key:  VTQCGUGRWZRRQX-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   24.1140  -10.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1128  -11.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8209  -11.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5305  -11.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5277  -10.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8191  -10.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2339  -10.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9431  -10.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6493  -10.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3591  -10.4275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6468   -9.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3625  -11.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6560  -11.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6590  -12.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3690  -12.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0773  -12.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0708  -11.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4029  -11.6732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4023  -12.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6955  -11.2640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9474  -11.2461    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
  2 18  1  0
 13 21  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251561

   (E)-N-(2-chlorophenyl)-3-(4-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: -1.46

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