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

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:32 UTC
Update Date2020-05-11 20:45:39 UTC
MCDB ID BMDB0004215
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1642190000-e16674c5bbe3fb0a7cb22014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1852290000-a6082a666145e38ac8c12014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1642190000-e16674c5bbe3fb0a7cb22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1852290000-a6082a666145e38ac8c12017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a42016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356c2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0490000000-72952d9b2b688fc509a42021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a702016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c812016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb32016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299c2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-3a7ce7071e05030e66db2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-2920000000-3df50fc6f200064ed5512021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9832326339909f0220922021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1950000000-cc84bd0a2d30854150842021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-1619a0f3fe3f1ff602a92021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0004215
DrugBank IDDB08399
Phenol Explorer Compound ID582
FoodDB 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)Download (PDF)
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 ]