3-(3,4-Dihydroxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide

ID: ALA68427

PubChem CID: 44308844

Max Phase: Preclinical

Molecular Formula: C15H13NO4

Molecular Weight: 271.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)Nc1cccc(O)c1

Standard InChI:  InChI=1S/C15H13NO4/c17-12-3-1-2-11(9-12)16-15(20)7-5-10-4-6-13(18)14(19)8-10/h1-9,17-19H,(H,16,20)/b7-5+

Standard InChI Key:  TUCRGTOIEKYIRD-FNORWQNLSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.1917   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -0.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  1  1  0
  5  2  2  0
  6 12  1  0
  7  4  1  0
  8 11  2  0
  9  7  2  0
 10  1  2  0
 11  5  1  0
 12 15  2  0
 13  9  1  0
 14  3  1  0
 15 11  1  0
 16  6  1  0
 17 13  1  0
 18 19  2  0
 19  7  1  0
 20 18  1  0
 20 13  2  0
  6  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA68427

   (E)-3-(3,4-dihydroxyphenyl)-N-(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: 271.27

Molecular Weight (Monoisotopic): 271.0845

AlogP: 2.46

#Rotatable Bonds: 3

Polar Surface Area: 89.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.92

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.51

Np Likeness Score: 0.03

References

1. Rajan P, Vedernikova I, Cos P, Berghe DV, Augustyns K, Haemers A..  (2001)  Synthesis and evaluation of caffeic acid amides as antioxidants.,  11  (2): [PMID:11206462] [10.1016/s0960-894x(00)00630-2]

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