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Showing Compound Theaflavin 3,3'-digallate (FDB002426)

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 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Theaflavin 3,3'-digallate is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), green tea, and black tea and in a lower concentration in red tea and herbal tea. Theaflavin 3,3'-digallate has also been detected, but not quantified in, german camomiles (Matricaria recutita) and peppermints (Mentha X piperita). This could make theaflavin 3,3'-digallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Theaflavin 3,3'-digallate.
CAS Number30462-35-2
Structure
Thumb
MOLSDFPDBSMILESInChI
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0900022140-a3678a36fc79ce49180f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0900021010-642658bbac11a52ce3812016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe0-0900020100-5a8de973a5f81304e2c42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0300000290-13d1ae4c2cef746693072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0900053670-4d7c62633c4cb9a81cc52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900021000-ab7a26951175749e28f02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000390-2097e10dcf73531bed162021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016s-0900001380-943b76021bce31ebea352021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900010320-aeb1efc5d743bc7895fa2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0000005190-fd060bbad6ef997dcf362021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gba-0500015290-51464f333dbd685127222021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdj-0803073980-f2ec77ed969a19fd11722021-09-25View Spectrum
NMRNot Available
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.