Showing Compound (E)-Resveratrol (FDB002451)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:23 UTC

Update date

2020-09-17 15:39:15 UTC

Primary ID

FDB002451

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(E)-Resveratrol

Description

Resveratrol, 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 lipid molecule. Resveratrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Resveratrol exists in all living species, ranging from bacteria to humans. Outside of the human body, Resveratrol is found, on average, in the highest concentration within red wines. Resveratrol has also been detected, but not quantified in, several different foods, such as purple mangosteens, sugar apples, chinese mustards, roselles, and pomegranates. This could make resveratrol a potential biomarker for the consumption of these foods. A resveratrol in which the double bond has E configuration.

CAS Number

501-36-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene	HMDB
(E)-3,4',5-Trihydroxystilbene	HMDB
(E)-3,4’,5-Trihydroxystilbene	HMDB
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol	ChEBI
(E)-5-(p-Hydroxystyryl)resorcinol	HMDB
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	PhytoBank
(e)-Resveratrol	ChEBI
3,4',5-Stilbenetriol	ChEBI
3,4',5-Trihydroxy-trans-stilbene	ChEBI
3,4',5-Trihydroxystilbene	ChEBI

Showing 1 to 10 of 30 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.46 m³·mol⁻¹	ChemAxon
Polarizability	24.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H12O3

IUPAC name

5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol

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 Key

LUKBXSAWLPMMSZ-OWOJBTEDSA-N

Isomeric SMILES

OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1

Average Molecular Weight

228.247

Monoisotopic Molecular Weight

228.078644246

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

resveratrol (CHEBI:45713 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C03582 )
Stilbenes (C03582 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090005 )

Ontology

Red wine

Fruits and vegetables:

Fruits:

Grapes

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 73.67%; H 5.30%; O 21.03%	DFC
Melting Point	Mp 265-267°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(E)-Resveratrol, 3 TMS, GC-MS Spectrum	splash10-0006-1853900000-4919511a11ec24935434	Spectrum
GC-MS	(E)-Resveratrol, non-derivatized, GC-MS Spectrum	splash10-0006-1853900000-4919511a11ec24935434	Spectrum
Predicted GC-MS	(E)-Resveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-0790000000-615dafbde185688e8755	Spectrum
Predicted GC-MS	(E)-Resveratrol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-8009800000-8b40ad68f231308861d4	Spectrum
Predicted GC-MS	(E)-Resveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 60V, Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 60V, Negative	splash10-014i-0900000000-9340e3fe04d435cf8475	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-00kf-0900000000-b0f6bf3388d96335d77e	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-1890000000-5a90c0c5508894cb16af	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-2910000000-e0183692948660939c19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0090000000-d9def7cee71fb7a40786	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004r-0970000000-f8c7ca07f27bfc1b8bda	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-b1333b06db343c38f529	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014l-0900000000-c856c7fa9653868e5785	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004r-0950000000-8e44b9aa58ac75282058	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000f-0900000000-2b750fcfd933ce8809f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-655581acb694e423a693	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0690000000-37f13318e23ebae81b00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-3910000000-e87807281eb836a65eb0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0d55e176d88ed31cd1cd	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190000000-cfdf20e77b23e0cc49e2	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a73-3930000000-243d9e319d0fee123dee	2016-08-04	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

GZM37-C:CLW14-F

EAFUS ID

Not Available

Dr. Duke ID

3,5,4'-TRIHYDROXYSTILBENE|TRANS-RESVERATROL|RESVERATROL

BIGG ID

Not Available

KNApSAcK ID

C00002903

HET ID

STL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Resveratrol

Phenol-Explorer Metabolite ID

580

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
5-hydroxyeicosatetraenoic-acid inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
5-hydroxytryptamine inhibitor	48279	Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.	DUKE
5-lipoxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
anti aggregant			DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti edemic			DUKE
anti eicosanoid	35222	A substance that diminishes the rate of a chemical reaction.	DUKE