Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:10:30 UTC
Primary IDFDB002426
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheaflavin 3,3'-digallate
DescriptionTheaflavin 3,3'-digallate belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Theaflavin 3,3'-digallate is an extremely weak basic (essentially neutral) compound (based on its pKa). Theaflavin 3,3'-digallate is found, on average, in the highest concentration within tea. Theaflavin 3,3'-digallate has also been detected, but not quantified in, german camomiles and peppermints. This could make theaflavin 3,3'-digallate a potential biomarker for the consumption of these foods.
CAS Number30462-35-2
Structure
Thumb
Synonyms
SynonymSource
Theaflavin 3,3'-digallic acidGenerator
Theaflavin 3,3'-di-O-gallateHMDB
2-{1-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulen-8-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Theaflavin 3,3'-digallatedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP3.78ALOGPS
logP6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.63ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area351.12 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity215.8 m³·mol⁻¹ChemAxon
Polarizability83.7 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC43H32O20
IUPAC name2-{8-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulen-1-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C43H32O20/c44-17-7-23(46)21-12-33(62-42(58)15-3-25(48)36(54)26(49)4-15)40(60-31(21)9-17)14-1-19-20(11-30(53)39(57)35(19)38(56)29(52)2-14)41-34(13-22-24(47)8-18(45)10-32(22)61-41)63-43(59)16-5-27(50)37(55)28(51)6-16/h1-11,33-34,40-41,44-51,53-55,57H,12-13H2,(H,52,56)
InChI KeyZEASWHWETFMWCV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=C2CC(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC2=C1)C1=CC(O)=C(O)C2=C1C=C(C=C(O)C2=O)C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight868.7022
Monoisotopic Molecular Weight868.148693464
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
  • Chromane
  • Benzopyran
  • Benzoate ester
  • 1-benzopyran
  • Benzoic acid or derivatives
  • Benzenetriol
  • Pyrogallol derivative
  • Tropolone
  • Tropone
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Cyclic ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.45%; H 3.71%; O 36.83%DFC
Melting PointMp 226-230° dec.DFC
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, Positivesplash10-0gbi-0900022140-a3678a36fc79ce49180fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0900021010-642658bbac11a52ce381JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe0-0900020100-5a8de973a5f81304e2c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0300000290-13d1ae4c2cef74669307JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0900053670-4d7c62633c4cb9a81cc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900021000-ab7a26951175749e28f0JSpectraViewer
ChemSpider ID2825757
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3589471
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID136
DrugBank IDNot Available
HMDB IDHMDB30551
CRC / DFC (Dictionary of Food Compounds) IDHHP83-R:CLS90-F
EAFUS IDNot Available
Dr. Duke IDTHEAFLAVIN-DIGALLATE|THEAFLAVIN-3-3'-DI-O-GALLATE
BIGG IDNot Available
KNApSAcK IDC00009351
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
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.