1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene

ID: ALA1094310

PubChem CID: 46210326

Max Phase: Preclinical

Molecular Formula: C20H24O2

Molecular Weight: 296.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C/C=C/CCCCc2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C20H24O2/c1-22-20-15-11-18(12-16-20)8-6-4-2-3-5-7-17-9-13-19(21)14-10-17/h4,6,9-16,21H,2-3,5,7-8H2,1H3/b6-4+

Standard InChI Key:  KKEWIPFKFMKFHF-GQCTYLIASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -2.9973    1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    1.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700    1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    2.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132    0.6982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274    1.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8571    2.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    1.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    2.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878    1.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008    2.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457    1.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1462    1.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613    0.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5695    1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918    0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  1  0
  2  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  5  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
  2  3  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094310

   4-[(E)-7-(4-methoxyphenyl)hept-5-enyl]phenol

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: 296.41

Molecular Weight (Monoisotopic): 296.1776

AlogP: 4.91

#Rotatable Bonds: 8

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: ┄

CX LogP: 5.91

CX LogD: 5.91

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 1.01

References

1. Wohlmuth H, Deseo MA, Brushett DJ, Thompson DR, Macfarlane G, Stevenson LM, Leach DN..  (2010)  Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E(2) inhibitory and cytotoxic activity.,  73  (4): [PMID:20297825] [10.1021/np900688r]

2. McLane RD, Le Cozannet-Laidin L, Boyle MS, Lanzillotta L, Taylor ZL, Anthony SR, Tranter M, Onorato AJ..  (2018)  Synthesis and PGE2 inhibitory activity of novel diarylheptanoids.,  28  (3): [PMID:29290543] [10.1016/j.bmcl.2017.12.046]

3. Vanucci-Bacqué C, Bedos-Belval F..  (2021)  Anti-inflammatory activity of naturally occuring diarylheptanoids - A review.,  31  [PMID:33422907] [10.1016/j.bmc.2020.115971]

Source

Source(1):

• Scientific Literature