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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:34 UTC
Update Date2022-03-07 02:53:35 UTC
HMDB IDHMDB0033070
Secondary Accession Numbers
  • HMDB33070
Metabolite Identification
Common NameTheaflavate A
DescriptionTheaflavate A, also known as theaflavic acid a, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Theaflavate A has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make theaflavate a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Theaflavate A.
Structure
Data?1563862348
Synonyms
ValueSource
Theaflavic acid aGenerator
2-(3,4-Dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 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]annulene-8-carboxylic acidHMDB
Chemical FormulaC43H32O19
Average Molecular Weight852.7028
Monoisotopic Molecular Weight852.153778842
IUPAC Name2-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 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]annulene-8-carboxylate
Traditional Name2-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 4-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-1,2,8-trihydroxy-9-oxobenzo[7]annulene-6-carboxylate
CAS Registry Number152542-70-6
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)C(=O)OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C43H32O19/c44-19-10-24(46)22-13-35(62-43(58)18-7-28(50)37(54)29(51)8-18)41(60-33(22)11-19)21-12-31(53)39(56)36-20(21)3-17(6-30(52)38(36)55)42(57)61-34-9-16-5-26(48)27(49)14-32(16)59-40(34)15-1-2-23(45)25(47)4-15/h1-8,10-12,14,34-35,40-41,44-51,53-54,56H,9,13H2,(H,52,55)
InChI KeyKGGRZHUCKSNYST-UHFFFAOYSA-N
Chemical Taxonomy
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
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Tropolone
  • Benzenetriol
  • Benzoic acid or derivatives
  • Tropone
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP3.98ALOGPS
logP6.38ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area330.89 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity213.32 m³·mol⁻¹ChemAxon
Polarizability83.79 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]+268.41430932474
DeepCCS[M-H]-266.51930932474
DeepCCS[M-2H]-300.43130932474
DeepCCS[M+Na]+274.45130932474
AllCCS[M+H]+271.332859911
AllCCS[M+H-H2O]+271.432859911
AllCCS[M+NH4]+271.232859911
AllCCS[M+Na]+271.232859911
AllCCS[M-H]-253.532859911
AllCCS[M+Na-2H]-256.732859911
AllCCS[M+HCOO]-260.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Theaflavate AOC1=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)C(=O)OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C(O)=C210128.6Standard polar33892256
Theaflavate AOC1=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)C(=O)OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C(O)=C26637.9Standard non polar33892256
Theaflavate AOC1=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)C(=O)OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C(O)=C28689.3Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 10V, Positive-QTOFsplash10-000i-0910010020-73dd3e70d78de18974742016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 20V, Positive-QTOFsplash10-0079-0900000000-75c8629c8ce8a6dc4ebc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 40V, Positive-QTOFsplash10-0079-2900000000-e5d42cca16e97425b32a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 10V, Negative-QTOFsplash10-0udi-0510031190-7a0936644b6071d77fc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 20V, Negative-QTOFsplash10-02dr-0910051730-b730837e0424d2d352082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 40V, Negative-QTOFsplash10-00or-0900010000-d2ccd7530f935cb7e2d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 10V, Positive-QTOFsplash10-0ul0-0040014290-8717009f297ebcf30cd92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 20V, Positive-QTOFsplash10-0w29-0851053690-c2cd9917f3ffa334c8222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 40V, Positive-QTOFsplash10-05tk-0950000520-f0b01669f7a4f7dbbf632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 10V, Negative-QTOFsplash10-0udi-0000002090-029241cadc186f187f3d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 20V, Negative-QTOFsplash10-0ugi-0710011290-0df105af280d8e3f6e3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Theaflavate A 40V, Negative-QTOFsplash10-05rr-0610000950-9b01f725189ff1e0a2872021-09-22Wishart 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 IDFDB011064
KNApSAcK IDC00057917
Chemspider ID35013538
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751367
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1833161
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:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Theaflavate A → 6,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 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]annulene-8-carboxylatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Theaflavate A → 6-[4-(3-{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]annulene-8-carbonyloxy}-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Theaflavate A → 6-[5-(3-{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]annulene-8-carbonyloxy}-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
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
Theaflavate A → Epitheaflavic acid 3'-gallatedetails
Theaflavate A → Theaflavate Bdetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Theaflavate A → [5-(3-{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]annulene-8-carbonyloxy}-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyphenyl]oxidanesulfonic aciddetails