3-hydroxy-cinnamanilide

ID: ALA2336362

PubChem CID: 71718276

Max Phase: Preclinical

Molecular Formula: C15H13NO2

Molecular Weight: 239.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(O)c1)Nc1ccccc1

Standard InChI:  InChI=1S/C15H13NO2/c17-14-8-4-5-12(11-14)9-10-15(18)16-13-6-2-1-3-7-13/h1-11,17H,(H,16,18)/b10-9+

Standard InChI Key:  BXDHXEGLUPHJCL-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   19.1242  -14.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1230  -14.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8311  -15.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5407  -14.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5379  -14.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8293  -13.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2441  -13.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9533  -14.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6595  -13.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3693  -14.1255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6570  -12.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4164  -13.7314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0753  -13.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7808  -14.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4863  -13.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4833  -12.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7689  -12.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0664  -12.9007    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA2336362

   3-HYDROXY-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: 239.27

Molecular Weight (Monoisotopic): 239.0946

AlogP: 3.04

#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: 3.27

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.81

Np Likeness Score: -0.40

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