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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 14:29:16 UTC
Update Date2020-02-26 21:25:02 UTC
HMDB IDHMDB0004215
Secondary Accession Numbers
  • HMDB04215
Metabolite Identification
Common Name3,3',4'5-Tetrahydroxystilbene
Description3,3',4'5-Tetrahydroxystilbene, also known as 3-hydroxyresveratol or piceatanol, 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. Thus, 3,3',4'5-tetrahydroxystilbene is considered to be an aromatic polyketide lipid molecule. 3,3',4'5-Tetrahydroxystilbene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3,3',4'5-Tetrahydroxystilbene exists in all living species, ranging from bacteria to humans. Outside of the human body, 3,3',4'5-Tetrahydroxystilbene has been detected, but not quantified in, several different foods, such as black tea, dessert wines, red champagnes, deerberries, and fruit juices. This could make 3,3',4'5-tetrahydroxystilbene a potential biomarker for the consumption of these foods. A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.
Structure
Data?1582752302
Synonyms
ValueSource
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
Chemical FormulaC14H12O4
Average Molecular Weight244.246
Monoisotopic Molecular Weight244.073558866
IUPAC Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Traditional Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
CAS Registry Number10083-24-6
SMILES
OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+164.29930932474
DeepCCS[M-H]-161.94130932474
DeepCCS[M-2H]-194.84930932474
DeepCCS[M+Na]+170.39230932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.532859911
AllCCS[M+NH4]+159.432859911
AllCCS[M+Na]+160.532859911
AllCCS[M-H]-154.832859911
AllCCS[M+Na-2H]-154.432859911
AllCCS[M+HCOO]-154.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,3',4'5-TetrahydroxystilbeneOC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C15063.0Standard polar33892256
3,3',4'5-TetrahydroxystilbeneOC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C12838.1Standard non polar33892256
3,3',4'5-TetrahydroxystilbeneOC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C12950.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O)=C2)=C12898.4Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C2=CC(O)=CC(O)=C2)=CC=C1O2809.7Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O2836.6Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #1C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O)=C2)=CC(O[Si](C)(C)C)=C12799.6Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)=C12768.8Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=C12763.7Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C2809.9Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #1C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)=CC(O[Si](C)(C)C)=C12750.0Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)=CC(O[Si](C)(C)C)=C12748.9Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=C12758.0Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,4TMS,isomer #1C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC(O[Si](C)(C)C)=C12802.4Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O)=C2)=C13188.5Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC(O)=CC(O)=C2)=CC=C1O3118.1Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O3137.3Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C13337.4Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)=C13336.2Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=C13320.2Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C1O[Si](C)(C)C(C)(C)C3374.9Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C13542.5Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C13523.3Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=C13539.7Semi standard non polar33892256
3,3',4'5-Tetrahydroxystilbene,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C13778.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS)splash10-001i-1642190000-e16674c5bbe3fb0a7cb22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS)splash10-001i-1852290000-a6082a666145e38ac8c12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized)splash10-001i-1642190000-e16674c5bbe3fb0a7cb22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized)splash10-001i-1852290000-a6082a666145e38ac8c12017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a42016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,3',4'5-Tetrahydroxystilbene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 35V, Negative-QTOFsplash10-0006-0490000000-72952d9b2b688fc509a42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Positive-QTOFsplash10-0002-0190000000-ba683912843d4fe87a702016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Positive-QTOFsplash10-0002-0690000000-84fddb6ca6d69b5c7c812016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Positive-QTOFsplash10-0pbi-4910000000-c3f282dac8a7f5eb07cd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Negative-QTOFsplash10-0006-0090000000-328195abcb348d62bbb32016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Negative-QTOFsplash10-0006-0190000000-1eebbf80fc971e14314b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Negative-QTOFsplash10-0m06-1960000000-bef8ef7244293d115d7c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Negative-QTOFsplash10-0006-0090000000-c3ceff739ebba19f299c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Negative-QTOFsplash10-0006-0390000000-3a7ce7071e05030e66db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Negative-QTOFsplash10-0597-2920000000-3df50fc6f200064ed5512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 10V, Positive-QTOFsplash10-0002-0190000000-9832326339909f0220922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 20V, Positive-QTOFsplash10-002b-1950000000-cc84bd0a2d30854150842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,3',4'5-Tetrahydroxystilbene 40V, Positive-QTOFsplash10-0a4i-1900000000-1619a0f3fe3f1ff602a92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
  • Platelet
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08399
Phenol Explorer Compound ID582
FooDB IDFDB023335
KNApSAcK IDC00002895
Chemspider ID581006
KEGG Compound IDC05901
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiceatannol
METLIN IDNot Available
PubChem Compound667639
PDB IDPIT
ChEBI ID28814
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBajaj, Renu; Gill, Mark T.; McLaughlin, Jerry L. Improved preparative synthesis of piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene). Revista Latinoamericana de Quimica (1987), 18(2), 79-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Palmieri L, Mameli M, Ronca G: Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. Drugs Exp Clin Res. 1999;25(2-3):79-85. [PubMed:10370868 ]
  2. Minuz P, Gaino S, Zuliani V, Tommasoli RM, Benati D, Ortolani R, Zancanaro C, Berton G, Santonastaso CL: Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha. Thromb Haemost. 2002 May;87(5):888-98. [PubMed:12038794 ]
  3. Geahlen RL, McLaughlin JL: Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem Biophys Res Commun. 1989 Nov 30;165(1):241-5. [PubMed:2590224 ]
  4. Maggiolini M, Recchia AG, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S: The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells. J Mol Endocrinol. 2005 Oct;35(2):269-81. [PubMed:16216908 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3,3',4'5-Tetrahydroxystilbene → 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-dioldetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,3',4'5-Tetrahydroxystilbene → 6-{5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,3',4'5-Tetrahydroxystilbene → 6-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,3',4'5-Tetrahydroxystilbene → 6-{4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3,3',4'5-Tetrahydroxystilbene → {5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenyl}oxidanesulfonic aciddetails