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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:34 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030551
Secondary Accession Numbers
  • HMDB30551
Metabolite Identification
Common 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.
Structure
Data?1563862002
Synonyms
ValueSource
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
Chemical FormulaC43H32O20
Average Molecular Weight868.7022
Monoisotopic Molecular Weight868.148693464
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
Traditional Name2-{8-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-5-oxobenzo[7]annulen-1-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number30462-35-2
SMILES
OC1=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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point226 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00045 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+272.05330932474
DeepCCS[M-H]-270.15830932474
DeepCCS[M-2H]-304.01930932474
DeepCCS[M+Na]+278.04930932474
AllCCS[M+H]+278.532859911
AllCCS[M+H-H2O]+278.432859911
AllCCS[M+NH4]+278.632859911
AllCCS[M+Na]+278.632859911
AllCCS[M-H]-267.632859911
AllCCS[M+Na-2H]-271.532859911
AllCCS[M+HCOO]-275.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Theaflavin 3,3'-digallateOC1=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)=C110237.6Standard polar33892256
Theaflavin 3,3'-digallateOC1=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)=C16603.8Standard non polar33892256
Theaflavin 3,3'-digallateOC1=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)=C18937.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 10V, Positive-QTOFsplash10-0gbi-0900022140-a3678a36fc79ce49180f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 20V, Positive-QTOFsplash10-0fe0-0900021010-642658bbac11a52ce3812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 40V, Positive-QTOFsplash10-0fe0-0900020100-5a8de973a5f81304e2c42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 10V, Negative-QTOFsplash10-014i-0300000290-13d1ae4c2cef746693072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 20V, Negative-QTOFsplash10-016r-0900053670-4d7c62633c4cb9a81cc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 40V, Negative-QTOFsplash10-00or-0900021000-ab7a26951175749e28f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 10V, Negative-QTOFsplash10-014i-0000000390-2097e10dcf73531bed162021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 20V, Negative-QTOFsplash10-016s-0900001380-943b76021bce31ebea352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 40V, Negative-QTOFsplash10-004i-0900010320-aeb1efc5d743bc7895fa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 10V, Positive-QTOFsplash10-014j-0000005190-fd060bbad6ef997dcf362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 20V, Positive-QTOFsplash10-0gba-0500015290-51464f333dbd685127222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavin 3,3'-digallate 40V, Positive-QTOFsplash10-0gdj-0803073980-f2ec77ed969a19fd11722021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002426
KNApSAcK IDC00009351
Chemspider ID2825757
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3589471
PDB IDNot Available
ChEBI ID975367
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1820951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Theaflavin 3,3'-digallate → Isotheaflavin 3'-gallatedetails
Theaflavin 3,3'-digallate → Neotheaflavin 3-gallatedetails