(E)-6-Fluoro-4-methoxy-2',3,5'-trihydroxystilbene

ID: ALA1817806

PubChem CID: 53379505

Max Phase: Preclinical

Molecular Formula: C15H13FO4

Molecular Weight: 276.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(F)c(/C=C/c2cc(O)ccc2O)cc1O

Standard InChI:  InChI=1S/C15H13FO4/c1-20-15-8-12(16)9(7-14(15)19)2-3-10-6-11(17)4-5-13(10)18/h2-8,17-19H,1H3/b3-2+

Standard InChI Key:  AURXEYYCUGNWLL-NSCUHMNNSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.6027    2.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853    1.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3160    1.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508    0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    0.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508    1.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720    2.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3160    0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503    2.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    2.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545    2.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713    3.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967    0.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4648    2.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709    1.7332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636    3.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807    2.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9032    3.3769    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  1  0
  8  3  2  0
  9  3  1  0
 10 13  2  0
 11  7  1  0
 12  7  2  0
 13 12  1  0
 14 11  2  0
  6  4  2  0
 14 10  1  0
  9 15  1  0
  2  1  2  0
  6 16  1  0
  3  1  1  0
 13 17  1  0
  4  5  1  0
 10 18  1  0
  5  9  2  0
 18 19  1  0
  6  8  1  0
 11 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1817806

   2-[(E)-2-(2-fluoro-5-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,4-diol

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: 276.26

Molecular Weight (Monoisotopic): 276.0798

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 69.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.88

CX Basic pKa: ┄

CX LogP: 3.39

CX LogD: 3.37

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.59

Np Likeness Score: 0.43

References

1. Albert S, Horbach R, Deising HB, Siewert B, Csuk R..  (2011)  Synthesis and antimicrobial activity of (E) stilbene derivatives.,  19  (17): [PMID:21803587] [10.1016/j.bmc.2011.07.015]

2. Csuk R, Albert S, Siewert B, Schwarz S..  (2012)  Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents.,  54  [PMID:22749392] [10.1016/j.ejmech.2012.06.015]

Source

Source(1):

• Scientific Literature