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Identification
Name Resveratrol
Accession Number DB02709 (EXPT02968)
Type small molecule
Groups experimental
Description

Resveratrol (3,5,4’-trihydroxystilbene) is a polyphenolic phytoalexin. It is a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. It exists as two structural isomers: cis-(Z) and trans-(E), with the trans-isomer shown in the top image. The trans- form can undergo isomerisation to the cis- form when heated or exposed to ultraviolet irradiation. In a 2004 issue of Science, Dr. Sinclair of Harvard University said resveratrol is not an easy molecule to protect from oxidation. It has been claimed that it is readily degraded by exposure to light, heat, and oxygen. However, studies find that Trans-resveratrol undergoes negligible oxidation in normal atmosphere at room temperature. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol
(E)-5-(p-Hydroxystyryl)resorcinol
(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzendiol
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol
(E)-resveratrol
3,4',5-Stilbenetriol
3,4',5-trihydroxy-stilbene
3,4',5-Trihydroxystilbene
trans-3,4',5-trihydroxystilbene
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Antioxidants
  • Platelet Aggregation Inhibitors
  • Enzyme Inhibitors
  • Anticarcinogenic Agents
  • Antineoplastic Agents, Phytogenic
  • Antimutagenic Agents
CAS number 501-36-0
Weight Average: 228.2433
Monoisotopic: 228.07864425
Chemical Formula C14H12O3
InChI Key InChIKey=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+
Plain Text
IUPAC Name
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
SMILES
OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Being investigated for the treatment of Herpes labialis infections (cold sores).
Pharmacodynamics Resveratrol, a phytoalexin, has been found to inhibit herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) replication in a dose-dependent, reversible manner, although this is only one of its many pharmaceutical properties. In some countries where there is higher consumption of red wine, there appears to be a lower incidence of heart disease. Other benefits of resveratrol include its anti-inflammatory and antioxidant effects. In preclinical studies, Resveratrol has been found to have potential anticancer properties.
Mechanism of action 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].
Absorption High absorption but very low bioavailability.
Volume of distribution Not Available
Protein binding Strong affinity towards protein binding.
Metabolism Hepatic. Rapidly metabolized and excreted.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 254 °C PhysProp
Predicted Properties
Property Value Source
water solubility 6.88e-02 g/l ALOGPS
logP 2.57 ALOGPS
logP 3.4 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 8.99 ChemAxon
pKa (strongest basic) -5.7 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 60.69 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 67.46 ChemAxon
polarizability 24.55 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Farina A, Ferranti C, Marra C: An improved synthesis of resveratrol. Nat Prod Res. 2006 Mar;20(3):247-52. Pubmed
  2. Renaud S, Ruf JC: The French paradox: vegetables or wine. Circulation. 1994 Dec;90(6):3118-9. Pubmed
  3. Wang Y, Catana F, Yang Y, Roderick R, van Breemen RB: An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and in wine. J Agric Food Chem. 2002 Jan 30;50(3):431-5. Pubmed
  4. Lyons MM, Yu C, Toma RB, Cho SY, Reiboldt W, Lee J, van Breemen RB: Resveratrol in raw and baked blueberries and bilberries. J Agric Food Chem. 2003 Sep 24;51(20):5867-70. Pubmed
  5. Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, Walle UK: High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos. 2004 Dec;32(12):1377-82. Epub 2004 Aug 27. Pubmed
  6. Csaki C, Keshishzadeh N, Fischer K, Shakibaei M: Regulation of inflammation signalling by resveratrol in human chondrocytes in vitro. Biochem Pharmacol. 2007 Sep 18;. Pubmed
  7. Docherty JJ, Fu MM, Stiffler BS, Limperos RJ, Pokabla CM, DeLucia AL: Resveratrol inhibition of herpes simplex virus replication. Antiviral Res. 1999 Oct;43(3):145-55. Pubmed
  8. N’ soukpoe-Kossi CN, St-Louis C, Beauregard M, Subirade M, Carpentier R, Hotchandani S, Tajmir-Riahi HA: Resveratrol binding to human serum albumin. J Biomol Struct Dyn. 2006 Dec;24(3):277-83. Pubmed
External Links
Resource Link
KEGG Compound C03582 Link_out
PubChem Compound 445154 Link_out
PubChem Substance 46504705 Link_out
ChemSpider 4880 Link_out
BindingDB 23926 Link_out
ChEBI 27881 Link_out
ChEMBL 27881 Link_out
Therapeutic Targets Database DNC001205 Link_out
PharmGKB PA165291843 Link_out
HET STL Link_out
Wikipedia http://en.wikipedia.org/wiki/Resveratrol Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (16.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Ribosyldihydronicotinamide dehydrogenase [quinone]

Pharmacological action: unknown

The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis

Organism class: human
UniProt ID: P16083 Link_out
Gene: NQO2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Buryanovskyy L, Fu Y, Boyd M, Ma Y, Hsieh TC, Wu JM, Zhang Z: Crystal structure of quinone reductase 2 in complex with resveratrol. Biochemistry. 2004 Sep 14;43(36):11417-26. Pubmed
  2. Wang Z, Hsieh TC, Zhang Z, Ma Y, Wu JM: Identification and purification of resveratrol targeting proteins using immobilized resveratrol affinity chromatography. Biochem Biophys Res Commun. 2004 Oct 22;323(3):743-9. Pubmed

2. Casein kinase II subunit alpha

Pharmacological action: unknown

Casein kinases are operationally defined by their preferential utilization of acidic proteins such as caseins as substrates. The alpha and alpha' chains contain the catalytic site. Participates in Wnt signaling. CK2 phosphorylates 'Ser-392' of p53/TP53 following UV irradiation

Organism class: human
UniProt ID: P68400 Link_out
Gene: CSNK2A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Prostaglandin G/H synthase 1

Pharmacological action: unknown
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Prostaglandin G/H synthase 2

Pharmacological action: unknown
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 1A2

Actions: substrate, inhibitor, inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Piver B, Fer M, Vitrac X, Merillon JM, Dreano Y, Berthou F, Lucas D: Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol. 2004 Aug 15;68(4):773-82. Pubmed
  2. Chang TK, Chen J, Lee WB: Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. J Pharmacol Exp Ther. 2001 Dec;299(3):874-82. Pubmed

2. Cytochrome P450 1A1

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chang TK, Chen J, Lee WB: Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. J Pharmacol Exp Ther. 2001 Dec;299(3):874-82. Pubmed
  2. Piver B, Fer M, Vitrac X, Merillon JM, Dreano Y, Berthou F, Lucas D: Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol. 2004 Aug 15;68(4):773-82. Pubmed

3. Cytochrome P450 1B1

Actions: inhibitor

Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development

UniProt ID: Q16678 Link_out
Gene: CYP1B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chang TK, Chen J, Lee WB: Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. J Pharmacol Exp Ther. 2001 Dec;299(3):874-82. Pubmed

4. Cytochrome P450 3A4

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chow HH, Garland LL, Hsu CH, Vining DR, Chew WM, Miller JA, Perloff M, Crowell JA, Alberts DS: Resveratrol modulates drug- and carcinogen-metabolizing enzymes in a healthy volunteer study. Cancer Prev Res (Phila). 2010 Sep;3(9):1168-75. Epub 2010 Aug 17. Pubmed
  2. Piver B, Berthou F, Dreano Y, Lucas D: Inhibition of CYP3A, CYP1A and CYP2E1 activities by resveratrol and other non volatile red wine components. Toxicol Lett. 2001 Dec 15;125(1-3):83-91. Pubmed
Carriers

1. Transthyretin

Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain

UniProt ID: P02766 Link_out
Gene: TTR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Commodari F, Khiat A, Ibrahimi S, Brizius AR, Kalkstein N: Comparison of the phytoestrogen trans-resveratrol (3,4’,5-trihydroxystilbene) structures from x-ray diffraction and solution NMR. Magn Reson Chem. 2005 Jul;43(7):567-72. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:21