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Showing Compound trans-resveratrol (FDB031212)

Record Information
Version1.0
Creation date2015-05-07 21:20:18 UTC
Update date2019-11-26 03:22:11 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(E)-Resveratrol, 3 TMS, GC-MS Spectrumsplash10-0006-1853900000-4919511a11ec24935434Spectrum
GC-MS(E)-Resveratrol, non-derivatized, GC-MS Spectrumsplash10-0006-1853900000-4919511a11ec24935434Spectrum
Predicted GC-MS(E)-Resveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0790000000-615dafbde185688e8755Spectrum
Predicted GC-MS(E)-Resveratrol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-8009800000-8b40ad68f231308861d4Spectrum
Predicted GC-MS(E)-Resveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-f9ff90d98488d6d055872017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd22017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-014i-0900000000-9340e3fe04d435cf84752017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00kf-0900000000-b0f6bf3388d96335d77e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-1890000000-5a90c0c5508894cb16af2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-2910000000-e0183692948660939c192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0090000000-d9def7cee71fb7a407862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-0970000000-f8c7ca07f27bfc1b8bda2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b1333b06db343c38f5292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c856c7fa9653868e57852017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-0950000000-8e44b9aa58ac752820582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000f-0900000000-2b750fcfd933ce8809f22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd22017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-655581acb694e423a6932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0690000000-37f13318e23ebae81b002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-3910000000-e87807281eb836a65eb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0d55e176d88ed31cd1cd2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-cfdf20e77b23e0cc49e22016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-3930000000-243d9e319d0fee123dee2016-08-04View Spectrum
NMRNot Available
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
Processing...
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