Record Information
Version1.0
Creation date2015-05-07 21:20:18 UTC
Update date2019-11-27 17:46:00 UTC
Primary IDFDB031212
Secondary Accession Numbers
  • FDB011814
  • FDB002451
Chemical Information
FooDB Nametrans-resveratrol
DescriptionResveratrol, also known as 3,4',5-trihydroxystilbene or trans-resveratrol, is a member of the class of compounds known as stilbenes. Stilbenes 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 lipid molecule. Resveratrol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Resveratrol is a bitter tasting compound and can be found in a number of food items such as broccoli, yellow wax bean, bilberry, and turnip, which makes resveratrol a potential biomarker for the consumption of these food products. Resveratrol can be found primarily in urine, as well as throughout most human tissues. Resveratrol exists in all eukaryotes, ranging from yeast to humans. Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or, when the plant is under attack by pathogens such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries . Resveratrol suppresses NF-kappaB (NF-kappaB) activation in HSV infected cells. Reports have indicated that HSV activates NF-kappaB during productive infection and this may be an essential aspect of its replication scheme [PMID: 9705914] (DrugBank).
CAS Number501-36-0
Structure
Thumb
Synonyms
SynonymSource
(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
trans-3,4',5 - TrihydroxystilbeneHMDB
Resveratrol-3-sulfateHMDB
SRT 501HMDB
SRT-501HMDB
cis-ResveratrolHMDB
trans-Resveratrol-3-O-sulfateHMDB
cis ResveratrolMeSH
trans Resveratrol 3 O sulfateMeSH
Resveratrol 3 sulfateMeSH
trans ResveratrolMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H12O3
IUPAC name5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1853900000-4919511a11ec24935434View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1853900000-4919511a11ec24935434View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0790000000-615dafbde185688e8755View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fr-8009800000-8b40ad68f231308861d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d05587View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0090000000-f9ff90d98488d6d05587View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-004i-0090000000-f9ff90d98488d6d05587View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d05587View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-014i-0900000000-9340e3fe04d435cf8475View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00kf-0900000000-b0f6bf3388d96335d77eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-1890000000-5a90c0c5508894cb16afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-2910000000-e0183692948660939c19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-d9def7cee71fb7a40786View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-0970000000-f8c7ca07f27bfc1b8bdaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b1333b06db343c38f529View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c856c7fa9653868e5785View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-0950000000-8e44b9aa58ac75282058View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-0900000000-2b750fcfd933ce8809f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-655581acb694e423a693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0690000000-37f13318e23ebae81b00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-3910000000-e87807281eb836a65eb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0d55e176d88ed31cd1cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-cfdf20e77b23e0cc49e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-3930000000-243d9e319d0fee123deeView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference