Piceatannol (YMDB01775)

Identification
YMDB IDYMDB01775
NamePiceatannol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-hydroxyresveratol
  • 3,3',4'5-Tetrahydroxystilbene
  • 3,4,3',5'-tetrahydroxy-trans-stilbene
  • 3,5,3',4'-tetrahydroxystilbene
  • 4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,2-diol
  • Piceatannol
  • 3,3',4',5-Tetrahydroxystilbene
  • 3,3',4,5'-Tetrahydroxy stilbene
  • RSVL-1
  • 3'-Hydroxyresveratol
  • 3,3',4,5'-Tetrahydroxystilbene
  • 3,5,3',4'-Tetrahydroxy-trans-stilbene
  • Astringinin
  • Demethyl isorhapontigenin
  • Piceatanol
  • 3,5,3',4'-Tetrahydroxy-stilbene
  • (E)-3,3',4,5'-Stilbenetetrol
  • (E)-3,3’,4,5’-Stilbenetetrol
  • 4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol
  • (E)-Piceatannol
  • Astringenin
  • trans-3,3',4,5'-Tetrahydroxystilbene
  • trans-3,3’,4,5’-Tetrahydroxystilbene
  • trans-Piceatannol
CAS number10083-24-6
WeightAverage: 244.2427
Monoisotopic: 244.073558872
InChI KeyCDRPUGZCRXZLFL-OWOJBTEDSA-N
InChIInChI=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+
IUPAC Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Traditional IUPAC Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Chemical FormulaC14H12O4
SMILESOC1=CC(\C=C\C2=CC=C(O)C(O)=C2)=CC(O)=C1
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
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1852290000-a6082a666145e38ac8c1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1852290000-a6082a666145e38ac8c1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0490000000-72952d9b2b688fc509a4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a70JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-3a7ce7071e05030e66dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-2920000000-3df50fc6f200064ed551JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9832326339909f022092JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1950000000-cc84bd0a2d3085415084JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-1619a0f3fe3f1ff602a9JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28814
HMDB IDHMDB04215
Pubchem Compound ID4813
Kegg IDC05901
ChemSpider ID581006
FOODB IDFDB023335
Wikipedia IDPiceatannol
BioCyc IDNot Available