(E)-3-(3,4-Dihydroxy-phenyl)-N-(2-hydroxy-phenyl)-acrylamide

ID: ALA421295

PubChem CID: 20196702

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)Nc1ccccc1O

Standard InChI:  InChI=1S/C15H13NO4/c17-12-4-2-1-3-11(12)16-15(20)8-6-10-5-7-13(18)14(19)9-10/h1-9,17-19H,(H,16,20)/b8-6+

Standard InChI Key:  REGRZFZFPDDXIW-SOFGYWHQSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.7875   -1.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -2.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -2.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  8  1  0
  6  4  2  0
  7 12  1  0
  8 11  2  0
  9  3  2  0
 10  2  2  0
 11  6  1  0
 12 14  2  0
 13  5  1  0
 14 11  1  0
 15  7  1  0
 16  9  1  0
 17  3  1  0
 18  9  1  0
 19 17  2  0
 20 19  1  0
 20 18  2  0
  7  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA421295

   (E)-3-(3,4-dihydroxyphenyl)-N-(2-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: 8.64

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.51

Np Likeness Score: -0.09

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