2-chloro-(4'-hydroxy)cinnamanilide

ID: ALA2336350

PubChem CID: 71717046

Max Phase: Preclinical

Molecular Formula: C15H12ClNO2

Molecular Weight: 273.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)Nc1ccccc1Cl

Standard InChI:  InChI=1S/C15H12ClNO2/c16-13-3-1-2-4-14(13)17-15(19)10-7-11-5-8-12(18)9-6-11/h1-10,18H,(H,17,19)/b10-7+

Standard InChI Key:  SWSHUSNBFAYRJI-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   27.3208  -11.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3197  -12.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0277  -12.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7374  -12.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7346  -11.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0259  -11.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4407  -11.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1500  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8561  -11.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5660  -11.7317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8536  -10.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2720  -11.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9775  -11.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6830  -11.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6800  -10.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9656  -10.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2630  -10.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6117  -12.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9788  -12.5453    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
  2 18  1  0
 13 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336350

   (E)-N-(2-chlorophenyl)-3-(4-hydroxyphenyl)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: 273.72

Molecular Weight (Monoisotopic): 273.0557

AlogP: 3.70

#Rotatable Bonds: 3

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.84

Np Likeness Score: -0.74

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. Shi ZH, Li NG, Shi QP, Tang H, Tang YP, Li W, Yin L, Yang JP, Duan JA..  (2013)  Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors.,  23  (5): [PMID:23375794] [10.1016/j.bmcl.2013.01.027]

Source

Source(1):

• Scientific Literature