3,3',4'5-Tetrahydroxystilbene (CHEM035652)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:57:36 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035652
Identification
Common Name3,3',4'5-Tetrahydroxystilbene
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5,3',4'-TetrahydroxystilbeneChEBI
3-HydroxyresveratolChEBI
4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diolChEBI
3,4,3',5'-Tetrahydroxy-trans-stilbeneHMDB
3,3',4',5-TetrahydroxystilbeneHMDB
3,3',4,5'-Tetrahydroxy stilbeneHMDB
RSVL-1HMDB
3'-HydroxyresveratolHMDB
3,3',4,5'-TetrahydroxystilbeneHMDB
3,5,3',4'-Tetrahydroxy-trans-stilbeneHMDB
AstringininHMDB
Demethyl isorhapontigeninHMDB
PiceatanolHMDB
3,5,3',4'-Tetrahydroxy-stilbeneHMDB
PiceatannolHMDB
3,3',4'5-TetrahydroxystilbeneChEBI
(E)-3,3',4,5'-StilbenetetrolPhytoBank
(E)-3,3’,4,5’-StilbenetetrolPhytoBank
4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediolPhytoBank
(E)-PiceatannolPhytoBank
AstringeninPhytoBank
trans-3,3',4,5'-TetrahydroxystilbenePhytoBank
trans-3,3’,4,5’-TetrahydroxystilbenePhytoBank
trans-PiceatannolPhytoBank
Chemical FormulaC14H12O4
Average Molecular Mass244.246 g/mol
Monoisotopic Mass244.074 g/mol
CAS Registry Number10083-24-6
IUPAC Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Traditional Name4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
SMILESOC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1
InChI IdentifierInChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+
InChI KeyCDRPUGZCRXZLFL-OWOJBTEDSA-N
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
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Resorcinol
  • Catechol
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP2.12ALOGPS
logP3.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.41ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.44 m³·mol⁻¹ChemAxon
Polarizability25.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-1852290000-a6082a666145e38ac8c1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1642190000-e16674c5bbe3fb0a7cb2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1852290000-a6082a666145e38ac8c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2000790000-bc4bda52250d1c2c356cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0490000000-72952d9b2b688fc509a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000000-3a7ce7071e05030e66dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-2920000000-3df50fc6f200064ed551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9832326339909f022092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1950000000-cc84bd0a2d3085415084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-1619a0f3fe3f1ff602a9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08399
HMDB IDHMDB0004215
FooDB IDFDB023335
Phenol Explorer ID582
KNApSAcK IDC00002895
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPIT
Wikipedia LinkPiceatannol
Chemspider ID581006
ChEBI ID28814
PubChem Compound ID667639
Kegg Compound IDC05901
YMDB IDYMDB01775
ECMDB IDM2MDB004897
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
2. Bajaj, Renu; Gill, Mark T.; McLaughlin, Jerry L. Improved preparative synthesis of piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene). Revista Latinoamericana de Quimica (1987), 18(2), 79-80.
3. Palmieri L, Mameli M, Ronca G: Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. Drugs Exp Clin Res. 1999;25(2-3):79-85.
4. Minuz P, Gaino S, Zuliani V, Tommasoli RM, Benati D, Ortolani R, Zancanaro C, Berton G, Santonastaso CL: Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha. Thromb Haemost. 2002 May;87(5):888-98.
5. Geahlen RL, McLaughlin JL: Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem Biophys Res Commun. 1989 Nov 30;165(1):241-5.
6. Maggiolini M, Recchia AG, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S: The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells. J Mol Endocrinol. 2005 Oct;35(2):269-81.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=10425214
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=10641182
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=11696049
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12044809
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15134373
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16455243
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17409035
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17698806
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18381677
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=19237510
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=19258424
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=19487074
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=19527681
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=20584749
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23185430
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23426871
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23713607
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23892029
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24470348
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24551719
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=24610083
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=24625210
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=24919577
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=25218158
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=25322988
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=25815690
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=25832644
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=25837778
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=26036705
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=26239705
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=26297476
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=26351210
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=26367737