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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB02709
rdf:type
n4:Drug
n4: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]
n4:generalReferences
# Farina A, Ferranti C, Marra C: An improved synthesis of resveratrol. Nat Prod Res. 2006 Mar;20(3):247-52. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16401555 # Renaud S, Ruf JC: The French paradox: vegetables or wine. Circulation. 1994 Dec;90(6):3118-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7994864 # 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":http://www.ncbi.nlm.nih.gov/pubmed/11804508 # 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":http://www.ncbi.nlm.nih.gov/pubmed/13129286 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15333514 # 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":http://www.ncbi.nlm.nih.gov/pubmed/17959154 # 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":http://www.ncbi.nlm.nih.gov/pubmed/10551373 # 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":http://www.ncbi.nlm.nih.gov/pubmed/17054386
n4:group
experimental investigational
n4:indication
Being investigated for the treatment of Herpes labialis infections (cold sores).
owl:sameAs
n18:DB02709 n19:DB02709
dcterms:title
Resveratrol
adms:identifier
n6:46504705 n7:STL n9:445154 n10:23926 n11:DB02709 n12:C03582 n13:27881 n14:4880 n15:PA165291843 n16:Resveratrol
n4:mechanismOfAction
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].
n4:synonym
3,4',5-trihydroxy-stilbene trans-3,4',5-trihydroxystilbene 3,4',5-Trihydroxystilbene (E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzendiol 3,4',5-Stilbenetriol (E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol (E)-5-(p-Hydroxystyryl)resorcinol (E)-5-(2-(4-hydroxyphenyl)ethenyl)-1,3-benzenediol (E)-resveratrol
n4:proteinBinding
Strong affinity towards protein binding.
n4:synthesisReference
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.
n20:hasConcept
n21:M0165532
n4:IUPAC-Name
n8:271B5101-363D-11E5-9242-09173F13E4C5
n4:InChI
n8:271B5107-363D-11E5-9242-09173F13E4C5
n4:Molecular-Formula
n8:271B5106-363D-11E5-9242-09173F13E4C5
n4:Molecular-Weight
n8:271B5103-363D-11E5-9242-09173F13E4C5
n4:Monoisotopic-Weight
n8:271B5104-363D-11E5-9242-09173F13E4C5
n4:SMILES
n8:271B5105-363D-11E5-9242-09173F13E4C5
n4:Water-Solubility
n8:271B50FF-363D-11E5-9242-09173F13E4C5
n4:logP
n8:271B50FD-363D-11E5-9242-09173F13E4C5 n8:271B5100-363D-11E5-9242-09173F13E4C5
n4:logS
n8:271B50FE-363D-11E5-9242-09173F13E4C5
n4:H-Bond-Acceptor-Count
n8:271B510D-363D-11E5-9242-09173F13E4C5
n4:H-Bond-Donor-Count
n8:271B510E-363D-11E5-9242-09173F13E4C5
n4:InChIKey
n8:271B5108-363D-11E5-9242-09173F13E4C5
n4:Polar-Surface-Area--PSA-
n8:271B5109-363D-11E5-9242-09173F13E4C5
n4:Polarizability
n8:271B510B-363D-11E5-9242-09173F13E4C5
n4:Refractivity
n8:271B510A-363D-11E5-9242-09173F13E4C5
n4:Rotatable-Bond-Count
n8:271B510C-363D-11E5-9242-09173F13E4C5
n4:absorption
High absorption but very low bioavailability.
n4:affectedOrganism
Humans and other mammals
n4:casRegistryNumber
501-36-0
n4:category
n4:Bioavailability
n8:271B5113-363D-11E5-9242-09173F13E4C5
n4:Ghose-Filter
n8:271B5115-363D-11E5-9242-09173F13E4C5
n4:MDDR-Like-Rule
n8:271B5116-363D-11E5-9242-09173F13E4C5
n4:Melting-Point
n8:271B5117-363D-11E5-9242-09173F13E4C5
n4:Number-of-Rings
n8:271B5112-363D-11E5-9242-09173F13E4C5
n4:Physiological-Charge
n8:271B5111-363D-11E5-9242-09173F13E4C5
n4:Rule-of-Five
n8:271B5114-363D-11E5-9242-09173F13E4C5
n4:Traditional-IUPAC-Name
n8:271B5102-363D-11E5-9242-09173F13E4C5
n4:pKa--strongest-acidic-
n8:271B510F-363D-11E5-9242-09173F13E4C5
n4:pKa--strongest-basic-
n8:271B5110-363D-11E5-9242-09173F13E4C5