(E)-3-(3,4-Dihydroxyphenyl)-N-p-tolylacrylamide

ID: ALA1165106

PubChem CID: 46703062

Max Phase: Preclinical

Molecular Formula: C16H15NO3

Molecular Weight: 269.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)/C=C/c2ccc(O)c(O)c2)cc1

Standard InChI:  InChI=1S/C16H15NO3/c1-11-2-6-13(7-3-11)17-16(20)9-5-12-4-8-14(18)15(19)10-12/h2-10,18-19H,1H3,(H,17,20)/b9-5+

Standard InChI Key:  LAIQRLYWSPLUFU-WEVVVXLNSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    9.9027  -11.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9016  -12.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6164  -13.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3328  -12.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3300  -11.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6146  -11.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1868  -13.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0429  -11.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7589  -11.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4718  -11.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1878  -11.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4687  -10.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1909  -12.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1882  -11.4793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4780  -13.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4807  -13.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1973  -14.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9126  -13.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9063  -13.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015  -15.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 10 12  2  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
  1 14  1  0
  2  7  1  0
 13 15  2  0
  3  4  2  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 13  1  0
  4  5  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1165106

   (E)-3-(3,4-dihydroxyphenyl)-N-(4-methylphenyl)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: 269.30

Molecular Weight (Monoisotopic): 269.1052

AlogP: 3.06

#Rotatable Bonds: 3

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.47

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.59

Np Likeness Score: -0.26

References

1. Fu J, Cheng K, Zhang ZM, Fang RQ, Zhu HL..  (2010)  Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials.,  45  (6): [PMID:20181415] [10.1016/j.ejmech.2010.01.066]

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