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

ID: ALA1165152

PubChem CID: 46703060

Max Phase: Preclinical

Molecular Formula: C16H15NO3

Molecular Weight: 269.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1NC(=O)/C=C/c1ccc(O)c(O)c1

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

Standard InChI Key:  PDBFFXOPMVKXDS-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -4.8556  -11.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568  -12.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1419  -12.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255  -12.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284  -11.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1437  -11.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5716  -12.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154  -11.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994  -11.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865  -11.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705  -11.5981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896  -10.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674  -12.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5702  -11.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803  -12.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776  -13.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5610  -14.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542  -13.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1480  -12.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591  -12.4101    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
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1165152

   (E)-3-(3,4-dihydroxyphenyl)-N-(2-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: -0.36

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