Phenethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate

ID: ALA4513485

PubChem CID: 8764348

Max Phase: Preclinical

Molecular Formula: C20H22O5

Molecular Weight: 342.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)OCCc2ccccc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H22O5/c1-22-17-13-16(14-18(23-2)20(17)24-3)9-10-19(21)25-12-11-15-7-5-4-6-8-15/h4-10,13-14H,11-12H2,1-3H3/b10-9+

Standard InChI Key:  GFTGHGIJVLPJJZ-MDZDMXLPSA-N

Molfile:  

 
     RDKit          2D

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   26.2838  -27.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9918  -27.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7015  -27.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6986  -26.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9900  -26.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4098  -27.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1169  -27.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8252  -27.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5323  -27.2619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8265  -28.4888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2406  -27.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9477  -27.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6561  -27.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6532  -28.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3607  -28.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0687  -28.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0648  -27.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3567  -27.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5757  -27.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8683  -27.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5771  -26.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5769  -25.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9876  -25.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6941  -24.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  2 20  1  0
 20 21  1  0
  1 22  1  0
 22 23  1  0
  6 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513485

   2-phenylethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.39

Molecular Weight (Monoisotopic): 342.1467

AlogP: 3.51

#Rotatable Bonds: 8

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 0.26

References

1. Gießel JM, Loesche A, Csuk R, Serbian I..  (2019)  Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase.,  177  [PMID:31158743] [10.1016/j.ejmech.2019.05.059]

2. Touaibia M, Faye DC, Doiron JA, Chiasson AI, Blanchard S, Roy PP, Surette ME..  (2022)  Structure-Activity Relationship Studies of New Sinapic Acid Phenethyl Ester Analogues Targeting the Biosynthesis of 5-Lipoxygenase Products: The Role of Phenolic Moiety, Ester Function, and Bioisosterism.,  85  (1.0): [PMID:34995066] [10.1021/acs.jnatprod.1c00982]

Source

Source(1):

• Scientific Literature