(E)-3,5-Diacetoxy-4'-fluorostilbene

ID: ALA551201

PubChem CID: 11186093

Max Phase: Preclinical

Molecular Formula: C18H15FO4

Molecular Weight: 314.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1cc(/C=C/c2ccc(F)cc2)cc(OC(C)=O)c1

Standard InChI:  InChI=1S/C18H15FO4/c1-12(20)22-17-9-15(10-18(11-17)23-13(2)21)4-3-14-5-7-16(19)8-6-14/h3-11H,1-2H3/b4-3+

Standard InChI Key:  HPVHEHSYYCPLKI-ONEGZZNKSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.2260    2.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5115    1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5115    0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2260    0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2260    3.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970    0.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6549    0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3694    0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838    0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7983    0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5128    0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5128   -0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7983   -0.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0838   -0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2272   -0.6666    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    3.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    4.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6549    3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970   -0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5115   -0.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0825   -0.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  1  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  3  8  1  0
 14 17  1  0
  7 18  1  0
  5  9  1  0
 18 19  2  0
  4  5  1  0
 18 20  1  0
  9 10  2  0
  8 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA551201

   [3-acetyloxy-5-[(E)-2-(4-fluorophenyl)ethenyl]phenyl] acetate

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: 314.31

Molecular Weight (Monoisotopic): 314.0954

AlogP: 3.85

#Rotatable Bonds: 4

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.49

Np Likeness Score: -0.14

References

1. Moran BW, Anderson FP, Devery A, Cloonan S, Butler WE, Varughese S, Draper SM, Kenny PT..  (2009)  Synthesis, structural characterisation and biological evaluation of fluorinated analogues of resveratrol.,  17  (13): [PMID:19481462] [10.1016/j.bmc.2009.05.007]

Source

Source(1):

• Scientific Literature