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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

Description

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.

CNS Activity

Originator

Approval Year

2011
562
Targets

Targets

Primary TargetPharmacologyConditionPotency
NAD-dependent protein deacetylase sirtuin-1
3
Target ID: Q96EB6
Gene ID: 23411.0
Gene Symbol: SIRT1
Target Organism: Homo sapiens (Human)
Binding Agent
1059
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
663
Unknown

Approved Use

Unknown
Palliative
Phase III
663
Unknown

Approved Use

Unknown
Primary
Phase III
663
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis.
2001
Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2).
2001
Downregulation of the cyclin D1/Cdk4 complex occurs during resveratrol-induced cell cycle arrest in colon cancer cell lines.
2001 Aug
The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp1a1 expression.
2001 Aug
Resveratrol exhibits cytostatic and antiestrogenic properties with human endometrial adenocarcinoma (Ishikawa) cells.
2001 Aug 15
Do wine polyphenols modulate p53 gene expression in human cancer cell lines?
2001 Jul
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
Resveratrol induces extensive apoptosis by depolarizing mitochondrial membranes and activating caspase-9 in acute lymphoblastic leukemia cells.
2001 Jun 15
Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts.
2001 Nov
Resveratrol-induced inactivation of human gastric adenocarcinoma cells through a protein kinase C-mediated mechanism.
2001 Nov 15
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
Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models.
2001 Oct 15
Involvement of c-jun NH(2)-terminal kinases in resveratrol-induced activation of p53 and apoptosis.
2002 Apr
Redox-sensitive interaction between KIAA0132 and Nrf2 mediates indomethacin-induced expression of gamma-glutamylcysteine synthetase.
2002 Apr 1
Gene expression profiles with activation of the estrogen receptor alpha-selective estrogen receptor modulator complex in breast cancer cells expressing wild-type estrogen receptor.
2002 Aug 1
Antioxidants induce different phenotypes by a distinct modulation of signal transduction.
2002 Dec 18
Mechanism of resveratrol-mediated suppression of tissue factor gene expression.
2002 Jan
Transcriptional induction of CYP1A1 by oltipraz in human Caco-2 cells is aryl hydrocarbon receptor- and calcium-dependent.
2002 Jul 5
Analysis of resveratrol-induced apoptosis in human B-cell chronic leukaemia.
2002 Jun
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
Flavonoid effects relevant to cancer.
2002 Nov
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
Resveratrol suppresses angiotensin II-induced Akt/protein kinase B and p70 S6 kinase phosphorylation and subsequent hypertrophy in rat aortic smooth muscle cells.
2002 Oct
Chronic treatment with trans resveratrol prevents intracerebroventricular streptozotocin induced cognitive impairment and oxidative stress in rats.
2002 Oct 11
Suppression of N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumorigenesis in F344 rats by resveratrol.
2002 Sep
Suppression of 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis in rats by resveratrol: role of nuclear factor-kappaB, cyclooxygenase 2, and matrix metalloprotease 9.
2002 Sep 1
Effects of resveratrol-related hydroxystilbenes on the nitric oxide production in macrophage cells: structural requirements and mechanism of action.
2002 Sep 13
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
Genome-scale analysis of resveratrol-induced gene expression profile in human ovarian cancer cells using a cDNA microarray.
2003 Apr
Effect of trans-resveratrol on signal transduction pathways involved in paclitaxel-induced apoptosis in human neuroblastoma SH-SY5Y cells.
2003 Apr
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 blocks interleukin-1beta-induced activation of the nuclear transcription factor NF-kappaB, inhibits proliferation, causes S-phase arrest, and induces apoptosis of acute myeloid leukemia cells.
2003 Aug 1
Phytoestrogen regulation of a Vitamin D3 receptor promoter and 1,25-dihydroxyvitamin D3 actions in human breast cancer cells.
2003 Feb
Suppression of IL-8 gene transcription by resveratrol in phorbol ester treated human monocytic cells.
2003 Jun
p21Cip1 gene expression is modulated by Egr1: a novel regulatory mechanism involved in the resveratrol antiproliferative effect.
2003 Jun 27
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.
2003 Mar
Red wine polyphenolics increase LDL receptor expression and activity and suppress the secretion of ApoB100 from human HepG2 cells.
2003 Mar
Differential expression of genes induced by resveratrol in LNCaP cells: P53-mediated molecular targets.
2003 Mar 20
Effects of resveratrol and 4-hexylresorcinol on hydrogen peroxide-induced oxidative DNA damage in human lymphocytes.
2003 May
Different short- and long-term effects of resveratrol on nuclear factor-kappaB phosphorylation and nuclear appearance in human endothelial cells.
2003 May
Resveratrol acts as an estrogen receptor (ER) agonist in breast cancer cells stably transfected with ER alpha.
2003 May 1
The egr-1 gene is induced by DNA-damaging agents and non-genotoxic drugs in both normal and neoplastic human cells.
2003 May 16
Oral administration of trans-resveratrol to guinea pigs increases cardiac DT-diaphorase and catalase activities, and protects isolated atria from menadione toxicity.
2003 May 2
Patents

Patents

JP2000069937A
2
JP2000256154A
2
JP2001002568A
2
JP2001058916A
2
JP2001072552A
3
JP2002293736A
2
JP2003300904A
2
JP2003513917A
2
JP2005017081A
2
JP2005023000A
2
JP2005143377A
2
JP2005281179A
2
JP2005306865A
2
JP2006067951A
5
JP2006273834A
2
JP2006347928A
2
JP2006505501A
2
JP2006528950A
2
JP2007119431A
4
JP2007126390A
2
JP2007145787A
2
JP2007145809A
2
JP2007505158A
9
JP2007505404A
2
JP2007513176A
2
JP2007513177A
2
JP2007513868A
2
JP2007514695A
4
JP2007517027A
4
JP2008231080A
2
JP2008253256A
2
JP2008255040A
2
JP2008266319A
5
JP2008510795A
75
JP2008513378A
16
JP2009013159A
2
JP2009165410A
2
JP2009173570A
2
JP2009234981A
2
JP2009501179A
2
JP2009523811A
2
JP2009531331A
6
JP2010024208A
2
JP2010043118A
2
JP2010124732A
2
JP2010148415A
4
JP2010202617A
2
JP2010270012A
2
JP2010529197A
3
JP2011046660A
2
JP2011057580A
2

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Wed Jul 05 23:50:40 UTC 2023
Edited
by admin
on Wed Jul 05 23:50:40 UTC 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
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 Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
DSLD 438 (Number of products:1077)
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
FDA ORPHAN DRUG 597817
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
NCI_THESAURUS C54630
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
FDA ORPHAN DRUG 241707
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
NCI_THESAURUS C275
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1602105
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
224
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
LACTMED
Resveratrol
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
PUBCHEM
445154
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
NSC
327430
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
EVMPD
SUB32889
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID4031980
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
NCI_THESAURUS
C1215
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
CHEBI
45713
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
CAS
501-36-0
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
HSDB
7571
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
RXCUI
1000492
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY RxNorm
MESH
C059514
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
SMS_ID
100000126143
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
FDA UNII
Q369O8926L
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
DRUG BANK
DB02709
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
WIKIPEDIA
RESVERATROL
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
DAILYMED
Q369O8926L
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
MERCK INDEX
M9549
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY Merck Index
CHEBI
27881
Created by admin on Wed Jul 05 23:50:41 UTC 2023 , Edited by admin on Wed Jul 05 23:50:41 UTC 2023
PRIMARY
Related Record Type Details
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4A1
TARGET -> INHIBITOR
Representative of PDE4
MRP-2
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.
MULTIDRUG RESISTANCE PROTEIN 1
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.
PAEONIA X SUFFRUTICOSA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
Stilbene was determined by means of of a newly developed rapid, sensitive, and accurate HPLC-DAD method.
CYTOCHROME P450 1B1
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
6β-hydroxylation of testosterone
IC50
NAD-DEPENDENT PROTEIN DEACYLASE SIRTUIN-5, MITOCHONDRIAL
TARGET -> ACTIVATOR
Resveratrol activates deacetylase activity while inhibiting desuccinylase activity.
OAT-1
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
OAT-3
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
CALCIUM/CALMODULIN-DEPENDENT 3',5'-CYCLIC NUCLEOTIDE PHOSPHODIESTERASE 1A
TARGET -> INHIBITOR
CGMP-INHIBITED 3',5'-CYCLIC PHOSPHODIESTERASE A
TARGET -> INHIBITOR
GRAPE
CONSTITUENT ALWAYS PRESENT -> PARENT
CYTOCHROME P450 3A4
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
SMILAX CHINA ROOT
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
Structure of PICEATANNOL
METABOLITE -> PARENT
Human liver microsomes (CYP1A2)
IN-VITRO
Scientific Literature
Structure of RESVERATROL-3-SULFATE
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of RESVERATROL
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
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HHS VULNERABILITY DISCLOSURE
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