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Identification
NameResveratrol
Accession NumberDB02709  (EXPT02968)
TypeSmall Molecule
GroupsExperimental, Investigational
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
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Co-veratrolHome Aide Diagnostics, Inc.
SaltsNot Available
Categories
UNIIQ369O8926L
CAS number501-36-0
WeightAverage: 228.2433
Monoisotopic: 228.07864425
Chemical FormulaC14H12O3
InChI KeyInChIKey=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
SMILES
OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
Taxonomy
DescriptionThis compound 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
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationBeing investigated for the treatment of Herpes labialis infections (cold sores).
PharmacodynamicsResveratrol, 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 actionResveratrol 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].
Related Articles
AbsorptionHigh absorption but very low bioavailability.
Volume of distributionNot Available
Protein bindingStrong affinity towards protein binding.
Metabolism

Hepatic. Rapidly metabolized and excreted.

SubstrateEnzymesProduct
Resveratrol
piceatannol (3,5,3',4'-tetrahydroxystilbene)Details
Resveratrol
tetrahydroxystilbene M1Details
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.59
Caco-2 permeable+0.8915
P-glycoprotein substrateNon-substrate0.6501
P-glycoprotein inhibitor INon-inhibitor0.9266
P-glycoprotein inhibitor IINon-inhibitor0.9612
Renal organic cation transporterNon-inhibitor0.8634
CYP450 2C9 substrateNon-substrate0.7519
CYP450 2D6 substrateNon-substrate0.9288
CYP450 3A4 substrateNon-substrate0.7143
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.7068
CYP450 2D6 inhibitorNon-inhibitor0.9226
CYP450 2C19 inhibitorInhibitor0.8052
CYP450 3A4 inhibitorInhibitor0.7539
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8559
Ames testNon AMES toxic0.8407
CarcinogenicityNon-carcinogens0.7825
BiodegradationNot ready biodegradable0.8499
Rat acute toxicity1.6791 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8933
hERG inhibition (predictor II)Non-inhibitor0.9462
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Capsuleoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point254 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0688 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.46 m3·mol-1ChemAxon
Polarizability24.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1853900000-4919511a11ec24935434View in MoNA
References
Synthesis Reference

Philippe Jeandet, Roger Bessis, Marielle Adrian, Jean-Claude Yvin, Jean-Marie Joubert, “Use of aluminium chloride as a resveratrol synthesis elicitor.” U.S. Patent US6080701, issued August, 1991.

US6080701
General References
  1. Farina A, Ferranti C, Marra C: An improved synthesis of resveratrol. Nat Prod Res. 2006 Mar;20(3):247-52. [PubMed:16401555 ]
  2. Renaud S, Ruf JC: The French paradox: vegetables or wine. Circulation. 1994 Dec;90(6):3118-9. [PubMed:7994864 ]
  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:11804508 ]
  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:13129286 ]
  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:15333514 ]
  6. Csaki C, Keshishzadeh N, Fischer K, Shakibaei M: Regulation of inflammation signalling by resveratrol in human chondrocytes in vitro. Biochem Pharmacol. 2008 Feb 1;75(3):677-87. Epub 2007 Sep 18. [PubMed:17959154 ]
  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:10551373 ]
  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:17054386 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (16.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nadph dehydrogenase (quinone) activity
Specific Function:
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.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular Weight:
25918.4 Da
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:15350128 ]
  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:15381063 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine kinase activity
Specific Function:
Catalytic subunit of a constitutively active serine/threonine-protein kinase complex that phosphorylates a large number of substrates containing acidic residues C-terminal to the phosphorylated serine or threonine. Regulates numerous cellular processes, such as cell cycle progression, apoptosis and transcription, as well as viral infection. May act as a regulatory node which integrates and coor...
Gene Name:
CSNK2A1
Uniprot ID:
P68400
Molecular Weight:
45143.25 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
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 N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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:15276085 ]
  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:11714871 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
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.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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:11714871 ]
  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:15276085 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
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, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
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:11714871 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1158/1940-6207.CAPR-09-0155. Epub 2010 Aug 17. [PubMed:20716633 ]
  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:11701226 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Identical protein binding
Specific Function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name:
TTR
Uniprot ID:
P02766
Molecular Weight:
15886.88 Da
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:15809979 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18