Record Information
Version1.0
Creation Date2016-09-30 23:05:59 UTC
Update Date2020-05-11 20:53:55 UTC
BMDB IDBMDB0003747
Secondary Accession Numbers
  • BMDB03747
Metabolite Identification
Common NameResveratrol
DescriptionResveratrol, also known as trans-resveratrol or SRT-501, 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, resveratrol is considered to be an aromatic polyketide. Resveratrol exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Resveratrol.
Structure
Thumb
Synonyms
ValueSource
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediolChEBI
(e)-ResveratrolChEBI
3,4',5-StilbenetriolChEBI
3,4',5-Trihydroxy-trans-stilbeneChEBI
3,4',5-TrihydroxystilbeneChEBI
3,5,4'-TrihydroxystilbeneChEBI
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diolChEBI
trans-ResveratrolKegg
SRT-501MeSH
trans ResveratrolMeSH
SRT 501MeSH
trans-3,4',5 - TrihydroxystilbeneHMDB
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)etheneHMDB
(E)-3,4',5-TrihydroxystilbeneHMDB
(E)-3,4’,5-TrihydroxystilbeneHMDB
(E)-5-(p-Hydroxystyryl)resorcinolHMDB
3,4’,5-StilbenetriolHMDB
3,4’,5-Trihydroxy-trans-stilbeneHMDB
3,4’,5-TrihydroxystilbeneHMDB
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediolHMDB
ResveratrolHMDB
trans-3,5,4'-TrihydroxystilbeneHMDB
trans-3,5,4’-TrihydroxystilbeneHMDB
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediolPhytoBank
Chemical FormulaC14H12O3
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
IUPAC Name5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Traditional Nameresveratrol
CAS Registry Number501-36-0
SMILES
OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
InChI Identifier
InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
InChI KeyLUKBXSAWLPMMSZ-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
  • 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
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.57ALOGPS
logP3.4ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.46 m³·mol⁻¹ChemAxon
Polarizability24.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003747
DrugBank IDDB02709
Phenol Explorer Compound ID592
FooDB IDFDB002451
KNApSAcK IDC00002903
Chemspider ID392875
KEGG Compound IDC03582
BioCyc IDCPD-83
BiGG IDNot Available
Wikipedia LinkResveratrol
METLIN IDNot Available
PubChem Compound445154
PDB IDNot Available
ChEBI ID45713
References
Synthesis ReferenceChen, Xin; Mei, Yicheng; Yu, Aimin; Wang, Kaiwen. Improved method for preparation of resveratrol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available