Record Information
Version1.0
Creation date2011-09-21 00:28:16 UTC
Update date2019-11-26 03:21:08 UTC
Primary IDFDB023335
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,3',4'5-Tetrahydroxystilbene
Description3,3',4'5-Tetrahydroxystilbene (or Piceatannol) is a phenolic stilbenoid. It is a metabolite of resveratrol found in red wine. A viral protein-tyrosine kinase (LMP2A) implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus, was recently found to be blocked by picetannol in vitro (PMID 2590224). Therefore there is research interest in piceatannol as an anti-cancer and anti-EBV drug. Piceatannol can also act as an agonist for estrogen receptor alpha in human breast cancer cells (PMID: 16216908). [HMDB]
CAS Number10083-24-6
Structure
Thumb
Synonyms
SynonymSource
3,5,3',4'-TetrahydroxystilbeneChEBI
3-HydroxyresveratolChEBI
4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diolChEBI
3,4,3',5'-Tetrahydroxy-trans-stilbeneHMDB
3,3',4',5-TetrahydroxystilbeneHMDB
3,3',4,5'-Tetrahydroxy stilbeneHMDB
RSVL-1HMDB
3'-HydroxyresveratolHMDB
3,3',4,5'-TetrahydroxystilbeneHMDB
3,5,3',4'-Tetrahydroxy-trans-stilbeneHMDB
AstringininHMDB
Demethyl isorhapontigeninHMDB
PiceatanolHMDB
3,5,3',4'-Tetrahydroxy-stilbeneHMDB
PiceatannolHMDB
3,3',4'5-TetrahydroxystilbeneChEBI
(E)-3,3',4,5'-StilbenetetrolPhytoBank
(E)-3,3’,4,5’-StilbenetetrolPhytoBank
4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediolPhytoBank
(E)-PiceatannolPhytoBank
AstringeninPhytoBank
trans-3,3',4,5'-TetrahydroxystilbenePhytoBank
trans-3,3’,4,5’-TetrahydroxystilbenePhytoBank
trans-PiceatannolPhytoBank
3,4,3',5'-tetrahydroxy-trans-stilbenehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP2.12ALOGPS
logP3.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.41ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.44 m³·mol⁻¹ChemAxon
Polarizability25.46 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H12O4
IUPAC name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
InChI IdentifierInChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+
InChI KeyCDRPUGZCRXZLFL-OWOJBTEDSA-N
Isomeric SMILESOC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1
Average Molecular Weight244.246
Monoisotopic Molecular Weight244.073558866
Classification
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Resorcinol
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3,3',4'5-Tetrahydroxystilbene, 4 TMS, GC-MS Spectrumsplash10-001i-1642190000-e16674c5bbe3fb0a7cb2Spectrum
GC-MS3,3',4'5-Tetrahydroxystilbene, 4 TMS, GC-MS Spectrumsplash10-001i-1852290000-a6082a666145e38ac8c1Spectrum
GC-MS3,3',4'5-Tetrahydroxystilbene, non-derivatized, GC-MS Spectrumsplash10-001i-1642190000-e16674c5bbe3fb0a7cb2Spectrum
GC-MS3,3',4'5-Tetrahydroxystilbene, non-derivatized, GC-MS Spectrumsplash10-001i-1852290000-a6082a666145e38ac8c1Spectrum
Predicted GC-MS3,3',4'5-Tetrahydroxystilbene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a4Spectrum
Predicted GC-MS3,3',4'5-Tetrahydroxystilbene, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356cSpectrum
Predicted GC-MS3,3',4'5-Tetrahydroxystilbene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,3',4'5-Tetrahydroxystilbene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0490000000-72952d9b2b688fc509a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c81Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-3a7ce7071e05030e66dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-2920000000-3df50fc6f200064ed551Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9832326339909f022092Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1950000000-cc84bd0a2d3085415084Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-1619a0f3fe3f1ff602a9Spectrum
NMRNot Available
ChemSpider ID581006
ChEMBL IDCHEMBL69863
KEGG Compound IDC05901
Pubchem Compound ID667639
Pubchem Substance IDNot Available
ChEBI ID28814
Phenol-Explorer ID582
DrugBank IDDB08399
HMDB IDHMDB04215
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPIT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPiceatannol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference