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Record Information
StatusDetected and Quantified
Creation Date2006-08-13 04:15:08 UTC
Update Date2022-03-07 02:49:19 UTC
Secondary Accession Numbers
  • HMDB03747
Metabolite Identification
Common NameResveratrol
DescriptionResveratrol is a polyphenolic phytoalexin. It is also classified as a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. The levels of resveratrol found in food vary greatly. Red wine contains between 0.2 and 5.8 mg/L depending on the grape variety, while white wine has much less. The reason for this difference is that red wine is fermented with grape skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed. Resveratrol is also sold as a nutritional supplement. A number of beneficial health effects, such as anti-cancer, antiviral, neuroprotective, anti-aging, anti-inflammatory, and life-prolonging effects have been reported for resveratrol. The fact that resveratrol is found in the skin of red grapes and as a constituent of red wine may explain the "French paradox". This paradox is based on the observation that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats. Resveratrol is thought to achieve these cardioprotective effects by a number of different routes: (1) inhibition of vascular cell adhesion molecule expression; (2) inhibition of vascular smooth muscle cell proliferation; (3) stimulation of endothelial nitric oxide synthase (eNOS) activity; (4) inhibition of platelet aggregation; and (5) inhibition of LDL peroxidation (PMID: 17875315 , 14676260 , 9678525 ). Resveratrol is a biomarker for the consumption of grapes and raisins.
trans ResveratrolMeSH
trans-3,4',5 - TrihydroxystilbeneHMDB
Chemical FormulaC14H12O3
Average Molecular Weight228.247
Monoisotopic Molecular Weight228.078644246
IUPAC Name5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Traditional Nameresveratrol
CAS Registry Number501-36-0
InChI Identifier
Chemical Taxonomy
Description 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
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
  • Stilbene
  • Styrene
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Not AvailableNot Available
Physical Properties
Experimental Molecular Properties
Melting Point254 °CNot Available
Boiling Point449.00 to 450.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility275 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.139 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility0.069 g/LALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.46 m³·mol⁻¹ChemAxon
Polarizability24.55 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices


MetaboliteSMILESKovats RI ValueColumn TypeReference
ResveratrolOC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C14788.5Standard polar33892256
ResveratrolOC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C12573.4Standard non polar33892256
ResveratrolOC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C12746.4Semi standard non polar33892256


Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Resveratrol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C12651.0Semi standard non polar33892256
Resveratrol,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C=C2)=C12621.9Semi standard non polar33892256
Resveratrol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C12614.2Semi standard non polar33892256
Resveratrol,2TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C12636.0Semi standard non polar33892256
Resveratrol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C12624.5Semi standard non polar33892256
Resveratrol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O)=C2)C=C12920.3Semi standard non polar33892256
Resveratrol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C2=CC=C(O)C=C2)=C12907.3Semi standard non polar33892256
Resveratrol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C13165.3Semi standard non polar33892256
Resveratrol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C13145.5Semi standard non polar33892256
Resveratrol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C13396.3Semi standard non polar33892256

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Resveratrol GC-MS (3 TMS)splash10-0006-1853900000-4919511a11ec249354342014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Resveratrol GC-MS (Non-derivatized)splash10-0006-1853900000-4919511a11ec249354342017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resveratrol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0790000000-615dafbde185688e87552016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resveratrol GC-MS (3 TMS) - 70eV, Positivesplash10-00fr-8009800000-8b40ad68f231308861d42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resveratrol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF , Negative-QTOFsplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 50V, Negative-QTOFsplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 60V, Negative-QTOFsplash10-004i-0090000000-f9ff90d98488d6d055872017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 20V, Negative-QTOFsplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 40V, Negative-QTOFsplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF , Negative-QTOFsplash10-004i-0090000000-f9ff90d98488d6d055872017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 50V, Negative-QTOFsplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd22017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 60V, Negative-QTOFsplash10-014i-0900000000-9340e3fe04d435cf84752017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 20V, Negative-QTOFsplash10-004i-0590000000-4a9b53d6aad6ed8189d22017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol ESI-TOF 40V, Negative-QTOFsplash10-00kf-0900000000-b0f6bf3388d96335d77e2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-qTof , Positive-QTOFsplash10-004i-1890000000-5a90c0c5508894cb16af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-qTof , Positive-QTOFsplash10-014i-2910000000-e0183692948660939c192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOFsplash10-004i-0090000000-d9def7cee71fb7a407862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOFsplash10-004r-0970000000-f8c7ca07f27bfc1b8bda2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-b1333b06db343c38f5292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QTOF , negative-QTOFsplash10-014l-0900000000-c856c7fa9653868e57852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QQ , negative-QTOFsplash10-004r-0950000000-8e44b9aa58ac752820582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-QQ , negative-QTOFsplash10-000f-0900000000-2b750fcfd933ce8809f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Resveratrol LC-ESI-TOF , negative-QTOFsplash10-014i-0900000000-79bf3bfcbb7bcdd0ffd22017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 10V, Positive-QTOFsplash10-004i-0090000000-655581acb694e423a6932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 20V, Positive-QTOFsplash10-004i-0690000000-37f13318e23ebae81b002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 40V, Positive-QTOFsplash10-014u-3910000000-e87807281eb836a65eb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 10V, Negative-QTOFsplash10-004i-0090000000-0d55e176d88ed31cd1cd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 20V, Negative-QTOFsplash10-004i-0190000000-cfdf20e77b23e0cc49e22016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resveratrol 40V, Negative-QTOFsplash10-0a73-3930000000-243d9e319d0fee123dee2016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
Normal Concentrations
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 592 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 592 details
UrineDetected and Quantified0.006 umol/mmol creatinineAdult (>18 years old)Both
UrineDetected and Quantified0.0156 +/- 0.0280 umol/mmol creatinineAdult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02709
Phenol Explorer Compound ID592
FooDB IDFDB002451
KNApSAcK IDC00002903
Chemspider ID392875
KEGG Compound IDC03582
BioCyc IDCPD-83
BiGG IDNot Available
Wikipedia LinkResveratrol
METLIN IDNot Available
PubChem Compound445154
PDB IDNot Available
ChEBI ID45713
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588831
Synthesis ReferenceChen, Xin; Mei, Yicheng; Yu, Aimin; Wang, Kaiwen. Improved method for preparation of resveratrol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. [PubMed:16988123 ]
  2. Olas B, Zbikowska HM, Wachowicz B, Krajewski T, Buczynski A, Magnuszewska A: Inhibitory effect of resveratrol on free radical generation in blood platelets. Acta Biochim Pol. 1999;46(4):961-6. [PubMed:10824865 ]
  3. Vilar S, Quezada E, Santana L, Uriarte E, Yanez M, Fraiz N, Alcaide C, Cano E, Orallo F: Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids. Bioorg Med Chem Lett. 2006 Jan 15;16(2):257-61. Epub 2005 Nov 3. [PubMed:16275073 ]
  4. Aggarwal BB, Bhardwaj A, Aggarwal RS, Seeram NP, Shishodia S, Takada Y: Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res. 2004 Sep-Oct;24(5A):2783-840. [PubMed:15517885 ]
  5. Olas B, Nowak P, Wachowicz B: Resveratrol protects against peroxynitrite-induced thiol oxidation in blood platelets. Cell Mol Biol Lett. 2004;9(4A):577-87. [PubMed:15647782 ]
  6. Kirk RI, Deitch JA, Wu JM, Lerea KM: Resveratrol decreases early signaling events in washed platelets but has little effect on platelet in whole blood. Blood Cells Mol Dis. 2000 Apr;26(2):144-50. [PubMed:11001623 ]
  7. Olas B, Wachowicz B, Majsterek I, Blasiak J: Resveratrol may reduce oxidative stress induced by platinum compounds in human plasma, blood platelets and lymphocytes. Anticancer Drugs. 2005 Jul;16(6):659-65. [PubMed:15930895 ]
  8. Anekonda TS: Resveratrol--a boon for treating Alzheimer's disease? Brain Res Rev. 2006 Sep;52(2):316-26. [PubMed:16766037 ]
  9. Miksits M, Maier-Salamon A, Aust S, Thalhammer T, Reznicek G, Kunert O, Haslinger E, Szekeres T, Jaeger W: Sulfation of resveratrol in human liver: evidence of a major role for the sulfotransferases SULT1A1 and SULT1E1. Xenobiotica. 2005 Dec;35(12):1101-19. [PubMed:16418064 ]
  10. Chun YJ, Kim MY, Guengerich FP: Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem Biophys Res Commun. 1999 Aug 19;262(1):20-4. [PubMed:10448061 ]
  11. Gester S, Wuest F, Pawelke B, Bergmann R, Pietzsch J: Synthesis and biodistribution of an 18F-labelled resveratrol derivative for small animal positron emission tomography. Amino Acids. 2005 Dec;29(4):415-28. Epub 2005 Jul 8. [PubMed:15997411 ]
  12. Fulda S, Debatin KM: Sensitization for tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis by the chemopreventive agent resveratrol. Cancer Res. 2004 Jan 1;64(1):337-46. [PubMed:14729643 ]
  13. Kimura Y, Okuda H: Resveratrol isolated from Polygonum cuspidatum root prevents tumor growth and metastasis to lung and tumor-induced neovascularization in Lewis lung carcinoma-bearing mice. J Nutr. 2001 Jun;131(6):1844-9. [PubMed:11385077 ]
  14. Gehm BD, McAndrews JM, Chien PY, Jameson JL: Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci U S A. 1997 Dec 9;94(25):14138-43. [PubMed:9391166 ]
  15. Bertelli AA, Giovannini L, Bernini W, Migliori M, Fregoni M, Bavaresco L, Bertelli A: Antiplatelet activity of cis-resveratrol. Drugs Exp Clin Res. 1996;22(2):61-3. [PubMed:8998912 ]
  16. Delmas D, Rebe C, Lacour S, Filomenko R, Athias A, Gambert P, Cherkaoui-Malki M, Jannin B, Dubrez-Daloz L, Latruffe N, Solary E: Resveratrol-induced apoptosis is associated with Fas redistribution in the rafts and the formation of a death-inducing signaling complex in colon cancer cells. J Biol Chem. 2003 Oct 17;278(42):41482-90. Epub 2003 Aug 5. [PubMed:12902349 ]
  17. Yanez M, Fraiz N, Cano E, Orallo F: Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem Biophys Res Commun. 2006 Jun 2;344(2):688-95. Epub 2006 Apr 17. [PubMed:16631124 ]
  18. Lee B, Moon SK: Resveratrol inhibits TNF-alpha-induced proliferation and matrix metalloproteinase expression in human vascular smooth muscle cells. J Nutr. 2005 Dec;135(12):2767-73. [PubMed:16317118 ]
  19. Aziz MH, Nihal M, Fu VX, Jarrard DF, Ahmad N: Resveratrol-caused apoptosis of human prostate carcinoma LNCaP cells is mediated via modulation of phosphatidylinositol 3'-kinase/Akt pathway and Bcl-2 family proteins. Mol Cancer Ther. 2006 May;5(5):1335-41. [PubMed:16731767 ]
  20. Zhuang H, Kim YS, Koehler RC, Dore S: Potential mechanism by which resveratrol, a red wine constituent, protects neurons. Ann N Y Acad Sci. 2003 May;993:276-86; discussion 287-8. [PubMed:12853318 ]
  21. Bass TM, Weinkove D, Houthoofd K, Gems D, Partridge L: Effects of resveratrol on lifespan in Drosophila melanogaster and Caenorhabditis elegans. Mech Ageing Dev. 2007 Oct;128(10):546-52. Epub 2007 Aug 14. [PubMed:17875315 ]
  22. Ferrieres J: The French paradox: lessons for other countries. Heart. 2004 Jan;90(1):107-11. [PubMed:14676260 ]
  23. Kopp P: Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the 'French paradox'? Eur J Endocrinol. 1998 Jun;138(6):619-20. [PubMed:9678525 ]


General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
Uniprot ID:
Molecular weight:
Resveratrol → 3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic aciddetails
Resveratrol → 6-{4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in zinc ion binding
Specific function:
NAD-dependent protein deacetylase that links transcriptional regulation directly to intracellular energetics and participates in the coordination of several separated cellular functions such as cell cycle, response to DNA damage, metobolism, apoptosis and autophagy. Can modulate chromatin function through deacetylation of histones and can promote alterations in the methylation of histones and DNA, leading to transcriptional repression. Deacetylates a broad range of transcription factors and coregulators, thereby regulating target gene expression positively and negatively. Serves as a sensor of the cytosolic ratio of NAD(+)/NADH which is altered by glucose deprivation and metabolic changes associated with caloric restriction. Is essential in skeletal muscle cell differentiation and in response to low nutrients mediates the inhibitory effect on skeletal myoblast differentiation which also involves 5'-AMP-activated protein kinase (AMPK) and nicotinamide phosphoribosyltransferase (NAMPT). Component of the eNoSC (energy-dependent nucleolar silencing) complex, a complex that mediates silencing of rDNA in response to intracellular energy status and acts by recruiting histone-modifying enzymes. The eNoSC complex is able to sense the energy status of cell: upon glucose starvation, elevation of NAD(+)/NADP(+) ratio activates SIRT1, leading to histone H3 deacetylation followed by dimethylation of H3 at 'Lys-9' (H3K9me2) by SUV39H1 and the formation of silent chromatin in the rDNA locus. Deacetylates 'Lys-266' of SUV39H1, leading to its activation. Inhibits skeletal muscle differentiation by deacetylating PCAF and MYOD1. Deacetylates H2A and 'Lys-26' of HIST1H1E. Deacetylates 'Lys-16' of histone H4 (in vitro). Involved in NR0B2/SHP corepression function through chromatin remodeling: Recruited to LRH1 target gene promoters by NR0B2/SHP thereby stimulating histone H3 and H4 deacetylation leading to transcriptional repression. Proposed to contribute to genomic integrity via positive regulation of telomere length; however, reports on localization to pericentromeric heterochromatin are conflicting. Proposed to play a role in constitutive heterochromatin (CH) formation and/or maintenance through regulation of the available pool of nuclear SUV39H1. Upon oxidative/metabolic stress decreases SUV39H1 degradation by inhibiting SUV39H1 polyubiquitination by MDM2. This increase in SUV39H1 levels enhances SUV39H1 turnover in CH, which in turn seems to accelerate renewal of the heterochromatin which correlates with greater genomic integrity during stress response. Deacetylates 'Lys-382' of p53/TP53 and impairs its ability to induce transcription-dependent proapoptotic program and modulate cell senescence. Deacetylates TAF1B and thereby represses rDNA transcription by the RNA polymerase I. Deacetylates MYC, promotes the association of MYC with MAX and decreases MYC stability leading to compromised transformational capability. Deacetylates FOXO3 in response to oxidative stress thereby increasing its ability to induce cell cycle arrest and resistance to oxidative stress but inhibiting FOXO3-mediated induction of apoptosis transcriptional activity; also leading to FOXO3 ubiquitination and protesomal degradation. Appears to have a similar effect on MLLT7/FOXO4 in regulation of transcriptional activity and apoptosis. Deacetylates DNMT1; thereby impairs DNMT1 methyltransferase-independent transcription repressor activity, modulates DNMT1 cell cycle regulatory function and DNMT1-mediated gene silencing. Deacetylates RELA/NF-kappa-B p65 thereby inhibiting its transactivating potential and augments apoptosis in response to TNF-alpha. Deacetylates HIF1A, KAT5/TIP60, RB1 and HIC1. Deacetylates FOXO1 resulting in its nuclear retention and enhancement of its transcriptional activity leading to increased gluconeogenesis in liver. Inhibits E2F1 transcriptional activity and apoptotic function, possibly by deacetylation. Involved in HES1- and HEY2-mediated transcriptional repression. In cooperation with MYCN seems to be involved in transcriptional repression of DUSP6/MAPK3 leading to MYCN stabilization by phosphorylation at 'Ser-62'. Deacetylates MEF2D. Required for antagonist-mediated transcription suppression of AR-dependent genes which may be linked to local deacetylation of histone H3. Represses HNF1A-mediated transcription. Required for the repression of ESRRG by CREBZF. Modulates AP-1 transcription factor activity. Deacetylates NR1H3 AND NR1H2 and deacetylation of NR1H3 at 'Lys-434' positively regulates transcription of NR1H3:RXR target genes, promotes NR1H3 proteosomal degradation and results in cholesterol efflux; a promoter clearing mechanism after reach round of transcription is proposed. Involved in lipid metabolism. Implicated in regulation of adipogenesis and fat mobilization in white adipocytes by repression of PPARG which probably involves association with NCOR1 and SMRT/NCOR2. Deacetylates ACSS2 leading to its activation, and HMGCS1. Involved in liver and muscle metabolism. Through deacteylation and activation of PPARGC1A is required to activate fatty acid oxidation in skeletel muscle under low-glucose conditions and is involved in glucose homeostasis. Involved in regulation of PPARA and fatty acid beta-oxidation in liver. Involved in positive regulation of insulin secretion in pancreatic beta cells in response to glucose; the function seems to imply transcriptional repression of UCP2. Proposed to deacetylate IRS2 thereby facilitating its insuline-induced tyrosine phosphorylation. Deacetylates SREBF1 isoform SREBP-1C thereby decreasing its stability and transactivation in lipogenic gene expression. Involved in DNA damage response by repressing genes which are involved in DNA repair, such as XPC and TP73, deacetylating XRCC6/Ku70, and faciliting recruitment of additional factors to sites of damaged DNA, such as SIRT1-deacetylated NBN can recruit ATM to initiate DNA repair and SIRT1-deacetylated XPA interacts with RPA2. Also involved in DNA repair of DNA double-strand breaks by homologous recombination and specifically single-strand annealing independently of XRCC6/Ku70 and NBN. Transcriptional suppression of XPC probably involves an E2F4:RBL2 suppressor complex and protein kinase B (AKT) signaling. Transcriptional suppression of TP73 probably involves E2F4 and PCAF. Deacetylates WRN thereby regulating its helicase and exonuclease activities and regulates WRN nuclear translocation in response to DNA damage. Deacetylates APEX1 at 'Lys-6' and 'Lys-7' and stimulates cellular AP endonuclease activity by promoting the association of APEX1 to XRCC1. Increases p53/TP53-mediated transcription-independent apoptosis by blocking nuclear translocation of cytoplasmic p53/TP53 and probably redirecting it to mitochondria. Deacetylates XRCC6/Ku70 at 'Lys-539' and 'Lys-542' causing it to sequester BAX away from mitochondria thereby inhibiting stress-induced apoptosis. Is involved in autophagy, presumably by deacetylating ATG5, ATG7 and MAP1LC3B/ATG8. Deacetylates AKT1 which leads to enhanced binding of AKT1 and PDK1 to PIP3 and promotes their activation. Proposed to play role in regulation of STK11/LBK1-dependent AMPK signaling pathways implicated in cellular senescence which seems to involve the regulation of the acetylation status of STK11/LBK1. Can deacetylate STK11/LBK1 and thereby increase its activity, cytoplasmic localization and association with STRAD; however, the relevance of such activity in normal cells is unclear. In endothelial cells is shown to inhibit STK11/LBK1 activity and to promote its degradation. Deacetylates SMAD7 at 'Lys-64' and 'Lys-70' thereby promoting its degradation. Deacetylates CIITA and augments its MHC class II transacivation and contributes to its stability. Deacteylates MECOM/EVI1. Isoform 2 is shown to deacetylate 'Lys-382' of p53/TP53, however with lower activity than isoform 1. In combination, the two isoforms exert an additive effect. Isoform 2 regulates p53/TP53 expression and cellular stress response and is in turn repressed by p53/TP53 presenting a SIRT1 isoform-dependent auto-regulatory loop. In case of HIV-1 infection, interacts with and deacetylates the viral Tat protein. The viral Tat protein inhibits SIRT1 deacetylation activity toward RELA/NF-kappa-B p65, thereby potentiates its transcriptional activity and SIRT1 is proposed to contribute to T-cell hyperactivation during infection. SirtT1 75 kDa fragment: catalytically inactive 75SirT1 may be involved in regulation of apoptosis. May be involved in protecting chondrocytes from apoptotic death by associating with cytochrome C and interfering with apoptosome assembly.
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General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
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Resveratrol → trans-Resveratrol 4'-sulfatedetails