Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:56 UTC
Primary IDFDB012512
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheaflavin 3'-gallate
DescriptionConstituent of black tea and commercial oolong tea Theaflavin-3-gallate is a theaflavin derivative.; Theaflavin-3-gallate is a theaflavins (a black tea extract) complex. It is one of the major black tea polyphenols. Research results show that it may be responsible for the chemopreventive activity in black tea extracts (PMID: 11103814). Theaflavin 3'-gallate is found in tea, german camomile, and peppermint.
CAS Number28543-07-9
Structure
Thumb
Synonyms
SynonymSource
Theaflavin 3'-gallic acidGenerator
Epitheaflavin monogallatebiospider
TF2Bbiospider
Theaflavin 3'-gallatedb_source
Theaflavin 3'-O-gallatebiospider
Theaflavin monogallate bbiospider
Theaflavin-3-gallatebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.03ALOGPS
logP4.41ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.58ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area284.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity180.03 m³·mol⁻¹ChemAxon
Polarizability69.87 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC36H28O16
IUPAC name(2R,3R)-5,7-dihydroxy-2-{3,4,6-trihydroxy-5-oxo-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-5H-benzo[7]annulen-1-yl}-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C36H28O16/c37-14-5-20(39)18-10-26(45)34(50-27(18)7-14)12-1-16-17(9-25(44)33(48)30(16)32(47)24(43)2-12)35-29(11-19-21(40)6-15(38)8-28(19)51-35)52-36(49)13-3-22(41)31(46)23(42)4-13/h1-9,26,29,34-35,37-42,44-46,48H,10-11H2,(H,43,47)/t26-,29-,34-,35-/m1/s1
InChI KeyGPLOTACQBREROW-WQLSNUALSA-N
Isomeric SMILESO[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC2=C(C(O)=C(O)C=C2[C@H]2OC3=C(C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=CC(O)=C3)C(=O)C(O)=C1
Average Molecular Weight716.5979
Monoisotopic Molecular Weight716.137734848
Classification
Description belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechin gallates
Alternative Parents
Substituents
  • Catechin gallate
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzopyran
  • Chromane
  • Benzoate ester
  • 1-benzopyran
  • Tropolone
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Tropone
  • Benzoyl
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 60.34%; H 3.94%; O 35.72%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbj-0900043500-ce6e88ff32b227cf2fd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900021000-66b5d462b429201c3264JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fka-1900011000-49f355bc749a5e0f33dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0500022900-b6f036e3840b4ccca887JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0170-0900154100-383ff8bd9da1ee6cbe55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-c9499715e20461d3070fJSpectraViewer
ChemSpider ID17216344
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22833650
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID135
DrugBank IDNot Available
HMDB IDHMDB05786
CRC / DFC (Dictionary of Food Compounds) IDHHP83-R:HHP85-T
EAFUS IDNot Available
Dr. Duke IDTHEAFLAVIN-3'-O-GALLATE|THEAFLAVIN-GALLATE-B|THEAFLAVIN-MONOGALLATE-B
BIGG IDNot Available
KNApSAcK IDC00009350
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTheaflavin-3-gallate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.