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

ID: ALA69803

PubChem CID: 13559594

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)Nc1ccc(O)cc1

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

Standard InChI Key:  QEFITTUAKPOZPK-KRXBUXKQSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.9042   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    0.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167    0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  2  2  0
  5  1  1  0
  6 10  1  0
  7  9  2  0
  8  1  2  0
  9  4  1  0
 10 14  2  0
 11  5  1  0
 12 18  1  0
 13  3  1  0
 14  9  1  0
 15  6  1  0
 16 11  2  0
 17 11  1  0
 18 17  2  0
 19 16  1  0
 20 12  1  0
 12 19  2  0
  6  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA69803

   (E)-3-(3,4-dihydroxyphenyl)-N-(4-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: 9.02

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.39

Np Likeness Score: 0.10

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