(E)-3-(2,5-Dihydroxy-phenyl)-acrylic acid phenethyl ester

ID: ALA131678

Cas Number: 179691-97-5

PubChem CID: 5909099

Max Phase: Preclinical

Molecular Formula: C17H16O4

Molecular Weight: 284.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)ccc1O)OCCc1ccccc1

Standard InChI:  InChI=1S/C17H16O4/c18-15-7-8-16(19)14(12-15)6-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-6+

Standard InChI Key:  OQKRMXDGEFRBAJ-RMKNXTFCSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    6.3667   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -6.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -4.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -6.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -5.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -6.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -4.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -7.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4792   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9625   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0000   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4792   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5167   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5167   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  2  2  0
  7  4  2  0
  8  5  2  0
  9  6  1  0
 10  4  1  0
 11  9  2  0
 12  5  1  0
 13  9  1  0
 14 10  1  0
 15 16  1  0
 16 14  1  0
 17 15  2  0
 18 15  1  0
 19 18  2  0
 20 17  1  0
 21 19  1  0
  8 11  1  0
 21 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA131678

   phenethyl (E)-3-(2,5-dihydroxyphenyl)prop-2-enoate

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: 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: 9.48

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.50

Np Likeness Score: 0.61

References

1. Burke TR, Fesen MR, Mazumder A, Wang J, Carothers AM, Grunberger D, Driscoll J, Kohn K, Pommier Y..  (1995)  Hydroxylated aromatic inhibitors of HIV-1 integrase.,  38  (21): [PMID:7473544] [10.1021/jm00021a006]

2. Buolamwini JK, Assefa H..  (2002)  CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.,  45  (4): [PMID:11831895] [10.1021/jm010399h]

3. 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