(E)-3-(3,4-Dihydroxyphenyl)-N-(4-methoxyphenyl)acrylamide

ID: ALA1163455

PubChem CID: 46861776

Max Phase: Preclinical

Molecular Formula: C16H15NO4

Molecular Weight: 285.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)/C=C/c2ccc(O)c(O)c2)cc1

Standard InChI:  InChI=1S/C16H15NO4/c1-21-13-6-4-12(5-7-13)17-16(20)9-3-11-2-8-14(18)15(19)10-11/h2-10,18-19H,1H3,(H,17,20)/b9-3+

Standard InChI Key:  MGXQKQSEWXXTPE-YCRREMRBSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.4569  -16.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4557  -17.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706  -17.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870  -17.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841  -16.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688  -16.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409  -17.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971  -16.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3131  -16.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0260  -16.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7420  -16.5356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0229  -15.3008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7451  -17.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7423  -16.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322  -17.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0349  -18.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7515  -19.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4667  -18.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605  -17.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7557  -19.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0433  -20.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 10 12  2  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
  1 14  1  0
  2  7  1  0
 13 15  2  0
  3  4  2  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 13  1  0
  4  5  1  0
 17 20  1  0
  9 10  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1163455

   N-(4-methoxyphenyl) caffeamide

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: 285.30

Molecular Weight (Monoisotopic): 285.1001

AlogP: 2.76

#Rotatable Bonds: 4

Polar Surface Area: 78.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.80

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: -0.13

References

1. 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]

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. Pillaiyar T, Namasivayam V, Manickam M, Jung SH..  (2018)  Inhibitors of Melanogenesis: An Updated Review.,  61  (17): [PMID:29763564] [10.1021/acs.jmedchem.7b00967]

Source

Source(1):

• Scientific Literature