Bovine Metabolome Database: Showing metabocard for Resveratrol (BMDB0003747)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:05:59 UTC

Update Date

2020-05-11 20:53:55 UTC

BMDB ID

BMDB0003747

Secondary Accession Numbers

BMDB03747

Metabolite Identification

Common Name

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. 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

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

Synonyms

Value	Source
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol	ChEBI
(e)-Resveratrol	ChEBI
3,4',5-Stilbenetriol	ChEBI
3,4',5-Trihydroxy-trans-stilbene	ChEBI
3,4',5-Trihydroxystilbene	ChEBI
3,5,4'-Trihydroxystilbene	ChEBI
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol	ChEBI
trans-Resveratrol	Kegg
SRT-501	MeSH
trans Resveratrol	MeSH
SRT 501	MeSH
trans-3,4',5 - Trihydroxystilbene	HMDB
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene	HMDB
(E)-3,4',5-Trihydroxystilbene	HMDB
(E)-3,4’,5-Trihydroxystilbene	HMDB
(E)-5-(p-Hydroxystyryl)resorcinol	HMDB
3,4’,5-Stilbenetriol	HMDB
3,4’,5-Trihydroxy-trans-stilbene	HMDB
3,4’,5-Trihydroxystilbene	HMDB
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	HMDB
Resveratrol	HMDB
trans-3,5,4'-Trihydroxystilbene	HMDB
trans-3,5,4’-Trihydroxystilbene	HMDB
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	PhytoBank

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.247

Monoisotopic Molecular Weight

228.078644246

IUPAC Name

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

Traditional Name

resveratrol

CAS Registry Number

501-36-0

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 Key

LUKBXSAWLPMMSZ-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.

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

Status

Detected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	254 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0006-1853900000-4919511a11ec24935434	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1853900000-4919511a11ec24935434	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0790000000-615dafbde185688e8755	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00fr-8009800000-8b40ad68f231308861d4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 60V, Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-f9ff90d98488d6d05587	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 60V, Negative	splash10-014i-0900000000-9340e3fe04d435cf8475	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0590000000-4a9b53d6aad6ed8189d2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-00kf-0900000000-b0f6bf3388d96335d77e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-1890000000-5a90c0c5508894cb16af	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-2910000000-e0183692948660939c19	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0090000000-d9def7cee71fb7a40786	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004r-0970000000-f8c7ca07f27bfc1b8bda	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-b1333b06db343c38f529	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014l-0900000000-c856c7fa9653868e5785	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004r-0950000000-8e44b9aa58ac75282058	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000f-0900000000-2b750fcfd933ce8809f2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0900000000-79bf3bfcbb7bcdd0ffd2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-655581acb694e423a693	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0690000000-37f13318e23ebae81b00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-3910000000-e87807281eb836a65eb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0d55e176d88ed31cd1cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190000000-cfdf20e77b23e0cc49e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a73-3930000000-243d9e319d0fee123dee	View in MoNA

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

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003747

DrugBank ID

DB02709

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Resveratrol

METLIN ID

Not Available

PubChem Compound

445154

PDB ID

Not Available

ChEBI ID

45713

References

Synthesis Reference

Chen, 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 References

Not Available

Showing metabocard for Resveratrol (BMDB0003747)

Structure for BMDB0003747 (Resveratrol)