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

ID: ALA275362

PubChem CID: 44271421

Max Phase: Preclinical

Molecular Formula: C15H13NO3

Molecular Weight: 255.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)Nc1ccccc1

Standard InChI:  InChI=1S/C15H13NO3/c17-13-8-6-11(10-14(13)18)7-9-15(19)16-12-4-2-1-3-5-12/h1-10,17-18H,(H,16,19)/b9-7+

Standard InChI Key:  WWYUUQYLTXYLBK-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.3542    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667    1.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500    2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667    1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -0.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042    2.3125    0.0000 C   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 13  2  0
 11  5  1  0
 12  3  1  0
 13  9  1  0
 14  6  1  0
 15 11  2  0
 16 11  1  0
 17 16  2  0
 18 15  1  0
 19 17  1  0
 18 19  2  0
  3  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA275362

   (E)-3-(3,4-dihydroxyphenyl)-N-phenylprop-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: 255.27

Molecular Weight (Monoisotopic): 255.0895

AlogP: 2.75

#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: 2.96

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.58

Np Likeness Score: -0.13

References

1. Nam NH, You YJ, Kim Y, Hong DH, Kim HM, Ahn BZ..  (2001)  Syntheses of certain 3-aryl-2-propenoates and evaluation of their cytotoxicity.,  11  (9): [PMID:11354370] [10.1016/s0960-894x(01)00165-2]

2. 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]

3. Jung M, Lee Y, Park M, Kim H, Kim H, Lim E, Tak J, Sim M, Lee D, Park N, Oh WK, Hur KY, Kang ES, Lee HC..  (2007)  Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors.,  17  (16): [PMID:17596944] [10.1016/j.bmcl.2007.06.016]

4. 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]

5. 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]

6. Misra K, Maity HS, Nag A, Sonawane A..  (2016)  Radical scavenging and antibacterial activity of caffemides against gram positive, gram negative and clinical drug resistance bacteria.,  26  (24): [PMID:27865704] [10.1016/j.bmcl.2016.10.089]

7. Jo H, Choi M, Sim J, Viji M, Li S, Lee YH, Kim Y, Seo SY, Zhou Y, Lee K, Kim WJ, Hong JT, Lee H, Jung JK..  (2017)  Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis.,  27  (15): [PMID:28619537] [10.1016/j.bmcl.2017.06.011]

8. Ullah S, Kang D, Lee S, Ikram M, Park C, Park Y, Yoon S, Chun P, Moon HR..  (2019)  Synthesis of cinnamic amide derivatives and their anti-melanogenic effect in α-MSH-stimulated B16F10 melanoma cells.,  161  [PMID:30347330] [10.1016/j.ejmech.2018.10.025]

Source

Source(1):

• Scientific Literature