Showing metabocard for 3,3',4'5-Tetrahydroxystilbene (BMDB0004215)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:32 UTC
Update Date2020-05-11 20:45:39 UTC
BMDB IDBMDB0004215
Secondary Accession Numbers
  • BMDB04215
Metabolite Identification
Common Name3,3',4'5-Tetrahydroxystilbene
DescriptionPiceatannol, also known as RSVL-1 or astringinin, 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, piceatannol is considered to be an aromatic polyketide lipid molecule. Piceatannol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Piceatannol exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1852290000-a6082a666145e38ac8c1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1852290000-a6082a666145e38ac8c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0490000000-72952d9b2b688fc509a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-3a7ce7071e05030e66dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-2920000000-3df50fc6f200064ed551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9832326339909f022092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1950000000-cc84bd0a2d3085415084View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-1619a0f3fe3f1ff602a9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004215
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
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)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]