(E)-N-Benzyl-3-(3,4-dihydroxy-phenyl)-acrylamide

ID: ALA67291

Cas Number: 100668-10-8

PubChem CID: 13644537

Max Phase: Preclinical

Molecular Formula: C16H15NO3

Molecular Weight: 269.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)NCc1ccccc1

Standard InChI:  InChI=1S/C16H15NO3/c18-14-8-6-12(10-15(14)19)7-9-16(20)17-11-13-4-2-1-3-5-13/h1-10,18-19H,11H2,(H,17,20)/b9-7+

Standard InChI Key:  JBDQTGJGXFAHIQ-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.0167   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -1.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -2.0625    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 10  1  0
  6  1  1  0
  7  9  2  0
  8  1  2  0
  9  4  1  0
 10 13  2  0
 11  6  1  0
 12  3  1  0
 13  9  1  0
 14  5  1  0
 15 11  1  0
 16 15  2  0
 17 15  1  0
 18 17  2  0
 19 16  1  0
 20 18  1  0
 20 19  2  0
  5  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA67291

   (E)-N-benzyl-3-(3,4-dihydroxyphenyl)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: 2.43

#Rotatable Bonds: 4

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: 2.67

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.59

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]

3. 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]

4. 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