2-chloro-(3'-hydroxy)cinnamanilide

ID: ALA2336789

PubChem CID: 71718291

Max Phase: Preclinical

Molecular Formula: C15H12ClNO2

Molecular Weight: 273.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(O)c1)Nc1ccccc1Cl

Standard InChI:  InChI=1S/C15H12ClNO2/c16-13-6-1-2-7-14(13)17-15(19)9-8-11-4-3-5-12(18)10-11/h1-10,18H,(H,17,19)/b9-8+

Standard InChI Key:  OMUJIZDFZQJYDG-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    9.0331  -29.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0319  -29.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7400  -30.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4496  -29.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4468  -29.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7382  -28.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1530  -28.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8622  -29.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5684  -28.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2782  -29.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5659  -27.8512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3253  -28.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9842  -28.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6897  -29.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3952  -28.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3923  -27.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6779  -27.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9753  -27.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6910  -29.8879    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
  1 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 14 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336789

   (E)-N-(2-chlorophenyl)-3-(3-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: 9.40

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.84

Np Likeness Score: -0.75

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