(E)-Phenethyl 3-(3,5-dihydroxyphenyl)acrylate

ID: ALA4476252

PubChem CID: 155538127

Max Phase: Preclinical

Molecular Formula: C17H16O4

Molecular Weight: 284.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)cc(O)c1)OCCc1ccccc1

Standard InChI:  InChI=1S/C17H16O4/c18-15-10-14(11-16(19)12-15)6-7-17(20)21-9-8-13-4-2-1-3-5-13/h1-7,10-12,18-19H,8-9H2/b7-6+

Standard InChI Key:  ZGNIBGAXWUVJKR-VOTSOKGWSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    8.5794   -5.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2944   -4.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096   -5.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096   -5.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2969   -6.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5794   -5.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2969   -7.1601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7245   -4.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4436   -5.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1586   -4.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8736   -5.0947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5885   -4.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3035   -5.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0227   -4.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0231   -3.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7355   -3.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4508   -3.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4530   -4.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7420   -5.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1586   -3.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644   -4.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 14 19  1  0
 10 20  2  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476252

   ---

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: 284.31

Molecular Weight (Monoisotopic): 284.1049

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.14

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.91

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: 0.55

References

1. Selka A, Doiron JA, Lyons P, Dastous S, Chiasson A, Cormier M, Turcotte S, Surette ME, Touaibia M..  (2019)  Discovery of a novel 2,5-dihydroxycinnamic acid-based 5-lipoxygenase inhibitor that induces apoptosis and may impair autophagic flux in RCC4 renal cancer cells.,  179  [PMID:31260889] [10.1016/j.ejmech.2019.06.060]

Source

Source(1):

• Scientific Literature