U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
587
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
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory effect of resveratrol on free radical generation in blood platelets.
1999
Cancer chemopreventive activity of resveratrol.
1999
Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells.
1999 Dec 1
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.
1999 Nov 26
Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity.
1999 Oct
Resveratrol reverses tumor-promoter-induced inhibition of gap-junctional intercellular communication.
2000 Sep 7
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Downregulation of the cyclin D1/Cdk4 complex occurs during resveratrol-induced cell cycle arrest in colon cancer cell lines.
2001 Aug
Differential response of immature rat uterine tissue to ethinylestradiol and the red wine constituent resveratrol.
2001 Jan
Do wine polyphenols modulate p53 gene expression in human cancer cell lines?
2001 Jul
Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models.
2001 Oct 15
Involvement of a post-transcriptional mechanism in the inhibition of CYP1A1 expression by resveratrol in breast cancer cells.
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
Antioxidants induce different phenotypes by a distinct modulation of signal transduction.
2002 Dec 18
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
Interactive gene expression pattern in prostate cancer cells exposed to phenolic antioxidants.
2002 Mar 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
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
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
p21Cip1 gene expression is modulated by Egr1: a novel regulatory mechanism involved in the resveratrol antiproliferative effect.
2003 Jun 27
Different short- and long-term effects of resveratrol on nuclear factor-kappaB phosphorylation and nuclear appearance in human endothelial cells.
2003 May
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
76
JP2008513378A
16
JP2009013159A
2
JP2009165410A
2
JP2009173570A
2
JP2009234981A
2
JP2009501179A
2
JP2009523811A
2
JP2009531331A
6
JP2010024208A
2
JP2010043118A
2
JP2010124732A
2
JP2010148415A
5
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.
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
ACTIVE MOIETY
Structure of RESVERATROL
METABOLITE (PARENT)
Structure of RESVERATROL-3-SULFATE
METABOLITE (PARENT)
Structure of PICEATANNOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966