Resveratrol (YMDB01780)

Identification

YMDB ID

YMDB01780

Name

Resveratrol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

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

3,4',5-Stilbenetriol
3,4',5-Trihydroxystilbene
3,5,4'-Trihydroxystilbene
cis-Resveratrol
Resveratrol-3-sulfate
SRT 501
SRT-501
trans-Resveratrol
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol
(e)-Resveratrol
3,4',5-Trihydroxy-trans-stilbene
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol
trans Resveratrol
trans-3,4',5 - Trihydroxystilbene
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene
(E)-3,4',5-Trihydroxystilbene
(E)-3,4’,5-Trihydroxystilbene
(E)-5-(p-Hydroxystyryl)resorcinol
3,4’,5-Stilbenetriol
3,4’,5-Trihydroxy-trans-stilbene
3,4’,5-Trihydroxystilbene
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol
Resveratrol
trans-3,5,4'-Trihydroxystilbene
trans-3,5,4’-Trihydroxystilbene
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol

CAS number

501-36-0

Weight

Average: 228.2433
Monoisotopic: 228.07864425

InChI Key

LUKBXSAWLPMMSZ-OWOJBTEDSA-N

InChI

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+

IUPAC Name

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

Traditional IUPAC Name

resveratrol

Chemical Formula

C₁₄H₁₂O₃

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

254 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB002451

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	36000
HMDB ID	HMDB03747
Pubchem Compound ID	5056
Kegg ID	C03582
ChemSpider ID	392875
FOODB ID	FDB002451
Wikipedia ID	Resveratrol
BioCyc ID	Not Available

Structure for #<Compound:0xa9f690ec>