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Human Metabolome Database Version 3.5

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Showing metabocard for Theaflavin-3-gallate (HMDB05786)

Record Information
Version 3.5
Creation Date 2007-01-22 06:34:18 -0700
Update Date 2013-02-08 17:14:18 -0700
HMDB ID HMDB05786
Secondary Accession Numbers None
Metabolite Identification
Common Name Theaflavin-3-gallate
Description 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Epitheaflavin monogallate
  2. TF2B
  3. Theaflavin monogallate b
  4. Theaflavin-3-gallate
Chemical Formula C36H28O16
Average Molecular Weight 716.5979
Monoisotopic Molecular Weight 716.137734848
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-2-yl}-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional IUPAC Name theaflavin-3-gallate
CAS Registry Number 28543-07-9
SMILES O[C@@H]1CC2=C(O[C@@H]1C1=CC3=C(C(O)=C(O)C(=C3)[C@H]3OC4=C(C[C@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)=CC(O)=C4)C(=O)C(O)=C1)C=C(O)C=C2O
InChI Identifier InChI=1S/C36H28O16/c37-15-6-20(39)17-10-25(44)34(50-26(17)8-15)13-1-12-2-19(30(45)33(48)29(12)32(47)24(43)3-13)35-28(11-18-21(40)7-16(38)9-27(18)51-35)52-36(49)14-4-22(41)31(46)23(42)5-14/h1-9,25,28,34-35,37-42,44-46,48H,10-11H2,(H,43,47)/t25-,28-,34-,35-/m1/s1
InChI Key AATSUYYYTHJRJO-RZYARBFNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Flavonoids
Sub Class Flavans
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diphenol
  • Alkyl Aryl Ether
  • Benzoate
  • Benzopyran
  • Benzoyl
  • Carboxylic Acid Ester
  • Chromane
  • Gallic Acid Derivative
  • Hydroxybenzoic Acid
  • Phenol
  • Phenol Derivative
  • Pyran
  • Pyrogallol Derivative
  • Resorcinol
  • Secondary Alcohol
  • Tropolone
  • Tropone
Direct Parent Flavanols
Ontology
Status Expected and Not Quantified
Origin
  • Food
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.08 g/L ALOGPS
LogP 3.06 ALOGPS
LogP 4.41 ChemAxon
LogS -3.95 ALOGPS
pKa (strongest acidic) 7.63 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Hydrogen Acceptor Count 15 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 284.36 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 180.03 ChemAxon
Polarizability 69.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID 135 Link_out
FoodDB ID FDB012512
KNApSAcK ID C00009350 Link_out
Chemspider ID 17216344 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Theaflavin-3-gallate Link_out
NuGOwiki Link HMDB05786 Link_out
Metagene Link HMDB05786 Link_out
METLIN ID Not Available
PubChem Compound 22833650 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Bryce, Thomas A.; Collier, Peter D.; Fowles, Ian; Thomas, Peter Edward; Frost, David; Wilkins, Cornelius K. Structures of the theaflavines of black tea. Tetrahedron Letters (1970), (32), 2789-92.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Lu J, Ho CT, Ghai G, Chen KY: Differential effects of theaflavin monogallates on cell growth, apoptosis, and Cox-2 gene expression in cancerous versus normal cells. Cancer Res. 2000 Nov 15;60(22):6465-71. Pubmed: 11103814 Link_out