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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O3
Molecular Weight 228.2433
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RESVERATROL

SMILES

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

InChI

InChIKey=LUKBXSAWLPMMSZ-OWOJBTEDSA-N
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+

HIDE SMILES / InChI

Molecular Formula C14H12O3
Molecular Weight 228.2433
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Resveratrol, a natural non-flavonoid polyphenol, exhibits a wide range of beneficial properties as an anticancer agent, a platelet anti-aggregation agent, and an antioxidant, as well as its anti-aging, anti-inflammatory, antiallergenic. This compound is in phase III clinical trials in combination with carboxymethyl-β-glucan for improving nasal symptoms in children with pollen-induced allergic rhinitis. Also in phase III clinical trial in the treatment of painful knee osteoarthritis and in type 2 diabetic patients. It has been demonstrated that resveratrol may prevent type 2 diabetic by targeting Sirtuin type 1 (SIRT1), indicating that SIRT1 may be a novel therapeutic target for diabetes prevention.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96EB6
Gene ID: 23411.0
Gene Symbol: SIRT1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of resveratrol on 12-O-tetradecanoylphorbol-13-acetate-induced oxidative events and gene expression in mouse skin.
1998 Dec 11
Inhibitory effect of resveratrol on free radical generation in blood platelets.
1999
Cancer chemopreventive activity of resveratrol.
1999
Effects of the wine polyphenolics quercetin and resveratrol on pro-inflammatory cytokine expression in RAW 264.7 macrophages.
1999 Apr 15
Cell cycle effects and control of gene expression by resveratrol in human breast carcinoma cell lines with different metastatic potentials.
1999 Aug
Resveratrol is a selective human cytochrome P450 1A1 inhibitor.
1999 Aug 19
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.
1999 Nov 26
Resveratrol inhibition of herpes simplex virus replication.
1999 Oct
Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity.
1999 Oct
Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol.
1999 Oct
Resveratrol prevents apoptosis in K562 cells by inhibiting lipoxygenase and cyclooxygenase activity.
1999 Oct 1
Ligand structure-dependent differences in activation of estrogen receptor alpha in human HepG2 liver and U2 osteogenic cancer cell lines.
2000 Apr 25
Chemopreventive properties of trans-resveratrol are associated with inhibition of activation of the IkappaB kinase.
2000 Jul 1
Resveratrol induces Fas signalling-independent apoptosis in THP-1 human monocytic leukaemia cells.
2000 May
Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure.
2000 May
Effects of resveratrol on the autophosphorylation of phorbol ester-responsive protein kinases: inhibition of protein kinase D but not protein kinase C isozyme autophosphorylation.
2000 Nov 1
Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway.
2000 Nov 15
Inhibition of dioxin effects on bone formation in vitro by a newly described aryl hydrocarbon receptor antagonist, resveratrol.
2000 Oct
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.
2000 Oct
Role of heme oxygenase-1 in the regulation of manganese superoxide dismutase gene expression in oxidatively-challenged astroglia.
2000 Oct
Resveratrol reverses tumor-promoter-induced inhibition of gap-junctional intercellular communication.
2000 Sep 7
Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis.
2001
Resveratrol exhibits cytostatic and antiestrogenic properties with human endometrial adenocarcinoma (Ishikawa) cells.
2001 Aug 15
Effect of resveratrol on the expression of autocrine growth modulators in human breast cancer cells.
2001 Dec
Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2.
2001 Dec
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.
2001 Feb
Resveratrol inhibits phorbol ester and UV-induced activator protein 1 activation by interfering with mitogen-activated protein kinase pathways.
2001 Jul
Resveratrol isolated from Polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice.
2001 Jun
Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers.
2001 Jun 1
Induction of endothelin-1 expression by oxidative stress in vascular smooth muscle cells.
2001 Nov-Dec
Bcl-2 overexpression attenuates resveratrol-induced apoptosis in U937 cells by inhibition of caspase-3 activity.
2001 Oct
Redox-sensitive interaction between KIAA0132 and Nrf2 mediates indomethacin-induced expression of gamma-glutamylcysteine synthetase.
2002 Apr 1
Mechanism of resveratrol-mediated suppression of tissue factor gene expression.
2002 Jan
An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and in wine.
2002 Jan 30
Transcriptional induction of CYP1A1 by oltipraz in human Caco-2 cells is aryl hydrocarbon receptor- and calcium-dependent.
2002 Jul 5
Resveratrol induces growth inhibition, S-phase arrest, apoptosis, and changes in biomarker expression in several human cancer cell lines.
2002 Mar
Resveratrol enhances the expression of non-steroidal anti-inflammatory drug-activated gene (NAG-1) by increasing the expression of p53.
2002 Mar
Resveratrol induces apoptosis in thyroid cancer cell lines via a MAPK- and p53-dependent mechanism.
2002 Mar
Interactive gene expression pattern in prostate cancer cells exposed to phenolic antioxidants.
2002 Mar 1
The antiproliferative activity of resveratrol results in apoptosis in MCF-7 but not in MDA-MB-231 human breast cancer cells: cell-specific alteration of the cell cycle.
2002 Nov 1
Chronic treatment with trans resveratrol prevents intracerebroventricular streptozotocin induced cognitive impairment and oxidative stress in rats.
2002 Oct 11
Resveratrol, a polyphenolic phytoalexin present in red wine, enhances expression and activity of endothelial nitric oxide synthase.
2002 Sep 24
Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.
2003
Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals.
2003 Apr 1
Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens.
2003 Apr 30
Resveratrol acts as an estrogen receptor (ER) agonist in breast cancer cells stably transfected with ER alpha.
2003 May 1
Patents

Sample Use Guides

Seasonal Allergic Rhinitis: 2 sprays per nostril 3 times a day for a period of two months knee osteoarthritis: resveratrol will be administered orally, at the dose of 40 mg (2 caplets) twice a day for one week, then at the dose of 20 mg (1 caplet) twice a day, for a total duration of 6 months.
Route of Administration: Other
The insulinoma cell line clone 1E (INS-1E) was treated with palmitic acid (PA). PA suppressed the expression of SIRT1 in a dose- and time-dependent manner. In PA-induced INS-1E cells, it was demonstrated that 10 µM resveratrol modulated the expression of PGC-1α and FOXO3a via SIRT1 and regulated the expression of mitochondrial biogenesis-associated, lipid metabolism-associated and β-cells-associated proteins.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:24:22 GMT 2023
Edited
by admin
on Fri Dec 15 16:24:22 GMT 2023
Record UNII
Q369O8926L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RESVERATROL
HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
Resveratrol [WHO-DD]
Common Name English
CA 1201
Common Name English
RESVERATROL(E)-FORM
Common Name English
RESVIDA
Common Name English
RESVERATROL [INCI]
Common Name English
5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL
Systematic Name English
TRANS-RESVERATROL [USP-RS]
Common Name English
BIOFORT
Common Name English
BIA-6-512
Code English
NSC-327430
Code English
RESVERATROL [MART.]
Common Name English
(E)-RESVERATROL
Common Name English
(E)-5-(P-HYDROXYSTYRYL)RESORCINOL
Common Name English
SRT 501M
Common Name English
TRANS-RESVERATROL
Common Name English
CUSPIDATIN
Common Name English
RESVERATROL P 5
Common Name English
Jotrol
Brand Name English
MELINJO RESVERATROL 20
Common Name English
BIA 6-512
Code English
POLYGONIN
Common Name English
RESVERATROL [HSDB]
Common Name English
RESVERATROL [VANDF]
Common Name English
5-((E)-2-(4-HYDROXYPHENYL)-ETHENYL) BENZENE-1,3 DIOL
Systematic Name English
RESVERATROL [MI]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1827
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
DSLD 438 (Number of products:1077)
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
FDA ORPHAN DRUG 597817
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
NCI_THESAURUS C54630
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
FDA ORPHAN DRUG 241707
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1602105
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
GRAS Notification (GRN No.)
224
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
LACTMED
Resveratrol
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
PUBCHEM
445154
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
NSC
327430
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
EVMPD
SUB32889
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID4031980
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
NCI_THESAURUS
C1215
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
CHEBI
45713
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
CAS
501-36-0
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
HSDB
7571
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
RXCUI
1000492
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY RxNorm
MESH
C059514
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
SMS_ID
100000126143
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
FDA UNII
Q369O8926L
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
DRUG BANK
DB02709
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
WIKIPEDIA
RESVERATROL
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
DAILYMED
Q369O8926L
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
MERCK INDEX
m9549
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY Merck Index
CHEBI
27881
Created by admin on Fri Dec 15 16:24:22 GMT 2023 , Edited by admin on Fri Dec 15 16:24:22 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Representative of PDE4
TRANSPORTER -> INHIBITOR
inhibited MTX efflux transport in MDR1-MDCK and MRP2-MDCK cellmonolayers, suggesting that the target of drug interaction wasMDR1 andMRP2 in the intestine duringthe absorption process.
TRANSPORTER -> INHIBITOR
inhibited MTX efflux transport in MDR1-MDCK and MRP2-MDCK cellmonolayers, suggesting that the target of drug interaction wasMDR1 andMRP2 in the intestine duringthe absorption process.
PARENT -> CONSTITUENT ALWAYS PRESENT
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METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
6β-hydroxylation of testosterone
IC50
TARGET -> ACTIVATOR
Resveratrol activates deacetylase activity while inhibiting desuccinylase activity.
TRANSPORTER -> INHIBITOR
MTX uptake was markedly inhibited by Res in rat kidney slicesand hOAT1/3-HEK293 cell, indicating that OAT1 and OAT3 were involved in the drug interaction in the kidney
TRANSPORTER -> INHIBITOR
MTX uptake was markedly inhibited by Res in rat kidney slicesand hOAT1/3-HEK293 cell, indicating that OAT1 and OAT3 were involved in the drug interaction in the kidney
TARGET -> INHIBITOR
TARGET -> INHIBITOR
CONSTITUENT ALWAYS PRESENT -> PARENT
METABOLIC ENZYME -> INHIBITOR
resveratrol inactivated CYP3A4 in a time- and NADPH-dependent manner, with rate (kinact) and affinity (equilibrium dissociation constant for enzyme-inhibitor complex; KI) of 0.2 min−1 and 20 μM, respectively
TIME-DEPENDENT INHIBITION
Ki
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
Activity against BACE-1 with Ki value of 5.4 x 10-6M and IC50 of 1.5 x 10-5M.
Related Record Type Details
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
Human liver microsomes (CYP1A2)
IN-VITRO
Scientific Literature
Related Record Type Details
ACTIVE MOIETY