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Showing Compound (Z)-Resveratrol (FDB012386)

Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2019-11-26 03:06:40 UTC
Primary IDFDB012386
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(Z)-Resveratrol
Description(Z)-Resveratrol, also known as cis-resveratrol, 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 (Z)-Resveratrol is an extremely weak basic (essentially neutral) compound (based on its pKa) (Z)-Resveratrol has been detected, but not quantified in, a few different foods, such as common grapes, nuts, and peanuts. This could make (Z)-resveratrol a potential biomarker for the consumption of these foods.
CAS Number61434-67-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(Z)-3,4',5-TrihydroxystilbeneChEBI
(Z)-3,5,4'-TrihydroxystilbeneChEBI
5-[(Z)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diolChEBI
cis-3,4',5-TrihydroxystilbeneChEBI
cis-3,5,4'-TrihydroxystilbeneChEBI
cis-3,4,5-TrihydroxystilbeneHMDB
cis-5-[2-(4-Hydroxyphenyl)ethenyl]benzene-1,3-diolHMDB
cis-ResveratrolHMDB
Z-ResveratrolHMDB
(Z)-ResveratrolChEBI
SRT 501MeSH
SRT-501MeSH
Resveratrol-3-sulfateMeSH
3,5,4'-TrihydroxystilbeneMeSH
trans-ResveratrolMeSH
trans-Resveratrol-3-O-sulfateMeSH
3,4',5-StilbenetriolMeSH
ResveratrolMeSH
trans ResveratrolMeSH
cis ResveratrolMeSH
3,4',5-TrihydroxystilbeneMeSH
trans Resveratrol 3 O sulfateMeSH
Resveratrol 3 sulfateMeSH
5-[(Z)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diolmanual
cis-5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diolmanual
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP2.57ALOGPS
logP3.4ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.46 m³·mol⁻¹ChemAxon
Polarizability23.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H12O3
IUPAC name5-[(Z)-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-UPHRSURJSA-N
Isomeric SMILES[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)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:

Biological location:

Source:

Role

Biological role:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.67%; H 5.30%; O 21.03%DFC
Melting PointMp 170-174°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data286 () (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-0211900000-e6c3f3295b4065e9aa2dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0211900000-e6c3f3295b4065e9aa2dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0790000000-615dafbde185688e8755JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fr-8009800000-8b40ad68f231308861d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-655581acb694e423a693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0690000000-37f13318e23ebae81b00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-3910000000-e87807281eb836a65eb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0d55e176d88ed31cd1cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-cfdf20e77b23e0cc49e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-3930000000-243d9e319d0fee123deeJSpectraViewer
ChemSpider ID1265933
ChEMBL IDCHEMBL87333
KEGG Compound IDNot Available
Pubchem Compound ID1548910
Pubchem Substance IDNot Available
ChEBI ID36002
Phenol-Explorer ID583
DrugBank IDNot Available
HMDB IDHMDB34118
CRC / DFC (Dictionary of Food Compounds) IDGZM37-C:HGS21-F
EAFUS IDNot Available
Dr. Duke IDCIS-RESVERATROL
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 IDResveratrol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).