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Showing metabocard for Epigallocatechin gallate (HMDB03153)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:36 -0600
Update Date 2013-02-08 17:12:19 -0700
HMDB ID HMDB03153
Secondary Accession Numbers None
Metabolite Identification
Common Name Epigallocatechin gallate
Description Epigallocatechin gallate (EGCG) is the principal catechin in tea from Camellia sinensis, the most consumed beverage worldwide (after water). Depending on brew time and temperature, a single cup of green tea may contain 100-200 mg EGCG. To control the dose of EGCG administered in experimental studies, green tea solids (GTS) or capsules of green tea extract standardized to EGCG content are often employed. However, there is considerable variability in the EGCG content of commercially available dietary supplements, ranging from 12-143% of the tablet or capsule weight. While standardizing tea preparations to EGCG or using highly purified EGCG for research presents an important strategy for the conduct of precise studies as well as the ability to replicate experiments, it is worth noting this approach limits the potential contributions and possible synergy with other bioactive tea ingredients, including caffeine and other flavonoids. Human studies of the bioavailability of green tea catechins reveal these compounds to be poorly absorbed, with <0.1% of ingested catechins appearing in blood. Most ingested EGCG is rapidly cleared from blood with an elimination half-life of {approx}3 h and preferentially excreted via bile to the colon. The growing interest in the role of EGCG in health promotion and disease prevention is reflected by an exponential growth of research publications in this field. (J Am Coll Nutr. 2007 Aug;26(4):362S-365S).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-Epigallocatechin gallat
  2. (-)-Epigallocatechin gallate
  3. (-)-Epigallocatechin-3-O-gallate
  4. (-)-Epigallocatechol gallate
  5. (-)-Epigallocatehin gallate
  6. Catechin deriv.
  7. EGCG
  8. Epigallocatcchin Gallate
  9. Epigallocate
  10. Epigallocatechin 3-gallate
  11. Epigallocatechin Gallate
  12. Epigallocic acid
  13. Galloyl-L-epigallocatechol
  14. Tea catechin
Chemical Formula C22H18O11
Average Molecular Weight 458.3717
Monoisotopic Molecular Weight 458.084911418
IUPAC Name (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional IUPAC Name epigallocatechin gallate
CAS Registry Number 989-51-5
SMILES OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1
InChI Identifier InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
InChI Key WMBWREPUVVBILR-WIYYLYMNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Polyketides
Class Flavonoids
Sub Class Flavans
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Flavans
  • Flavans, Flavanols and Leucoanthocyanidins(Lipidmaps)
Substituents
  • 1,2 Diphenol
  • Alkyl Aryl Ether
  • Benzoate
  • Benzopyran
  • Benzoyl
  • Carboxylic Acid Ester
  • Catechin
  • Chromane
  • Epigallocatechin
  • Flavanol
  • Gallic Acid Derivative
  • Hydroxybenzoic Acid
  • Phenol
  • Phenol Derivative
  • Pyran
  • Pyrogallol Derivative
  • Resorcinol
Direct Parent Catechin Gallates
Ontology
Status Expected and Not Quantified
Origin
  • Plant
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 140 - 142 °C 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 0.073 g/L ALOGPS
LogP 2.38 ALOGPS
LogP 3.08 ChemAxon
LogS -3.80 ALOGPS
pKa (strongest acidic) 7.99 ChemAxon
pKa (strongest basic) -5.4 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 197.37 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 111.75 ChemAxon
Polarizability 43.27 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Fibroblasts
  • Neuron
  • Kidney
  • Liver
  • Prostate
  • Skin
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 129
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 129 Link_out
Phenol Explorer Metabolite ID 129 Link_out
FoodDB ID FDB017702
KNApSAcK ID C00000958 Link_out
Chemspider ID 58575 Link_out
KEGG Compound ID C09731 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Epigallocatechin gallate Link_out
NuGOwiki Link HMDB03153 Link_out
Metagene Link HMDB03153 Link_out
METLIN ID 3550 Link_out
PubChem Compound 65064 Link_out
PDB ID EGG Link_out
ChEBI ID 4806 Link_out
References
Synthesis Reference Liang, Huiling; Liang, Yuerong; Dong, Junjie; Lu, Jianliang. Tea extraction methods in relation to control of epimerization of tea catechins. Journal of the Science of Food and Agriculture (2007), 87(9), 1748-1752.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Uchida S, Ozaki M, Suzuki K, Shikita M: Radioprotective effects of (-)-epigallocatechin 3-O-gallate (green-tea tannin) in mice. Life Sci. 1992;50(2):147-52. Pubmed: 1731169 Link_out
  2. Dashwood WM, Carter O, Al-Fageeh M, Li Q, Dashwood RH: Lysosomal trafficking of beta-catenin induced by the tea polyphenol epigallocatechin-3-gallate. Mutat Res. 2005 Dec 11;591(1-2):161-72. Epub 2005 Jul 27. Pubmed: 16054165 Link_out
  3. Dorchies OM, Wagner S, Vuadens O, Waldhauser K, Buetler TM, Kucera P, Ruegg UT: Green tea extract and its major polyphenol (-)-epigallocatechin gallate improve muscle function in a mouse model for Duchenne muscular dystrophy. Am J Physiol Cell Physiol. 2006 Feb;290(2):C616-25. Pubmed: 16403950 Link_out
  4. Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70. Pubmed: 12832052 Link_out
  5. Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43. Pubmed: 16772446 Link_out
  6. Suganuma M, Okabe S, Sueoka N, Sueoka E, Matsuyama S, Imai K, Nakachi K, Fujiki H: Green tea and cancer chemoprevention. Mutat Res. 1999 Jul 16;428(1-2):339-44. Pubmed: 10518005 Link_out
  7. Katiyar SK, Afaq F, Perez A, Mukhtar H: Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. Carcinogenesis. 2001 Feb;22(2):287-94. Pubmed: 11181450 Link_out
  8. Meng X, Sang S, Zhu N, Lu H, Sheng S, Lee MJ, Ho CT, Yang CS: Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats. Chem Res Toxicol. 2002 Aug;15(8):1042-50. Pubmed: 12184788 Link_out
  9. Shirai T, Reshad K, Yoshitomi A, Chida K, Nakamura H, Taniguchi M: Green tea-induced asthma: relationship between immunological reactivity, specific and non-specific bronchial responsiveness. Clin Exp Allergy. 2003 Sep;33(9):1252-5. Pubmed: 12956747 Link_out
  10. Fujiki H, Suganuma M, Okabe S, Sueoka N, Komori A, Sueoka E, Kozu T, Tada Y, Suga K, Imai K, Nakachi K: Cancer inhibition by green tea. Mutat Res. 1998 Jun 18;402(1-2):307-10. Pubmed: 9675322 Link_out
  11. Wang YC, Bachrach U: The specific anti-cancer activity of green tea (-)-epigallocatechin-3-gallate (EGCG). Amino Acids. 2002;22(2):131-43. Pubmed: 12395181 Link_out
  12. Katiyar SK, Matsui MS, Elmets CA, Mukhtar H: Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leukocytes in human skin. Photochem Photobiol. 1999 Feb;69(2):148-53. Pubmed: 10048310 Link_out
  13. Shirai T, Sato A, Chida K, Hayakawa H, Akiyama J, Iwata M, Taniguchi M, Reshad K, Hara Y: Epigallocatechin gallate-induced histamine release in patients with green tea-induced asthma. Ann Allergy Asthma Immunol. 1997 Jul;79(1):65-9. Pubmed: 9236503 Link_out
  14. Caporali A, Davalli P, Astancolle S, D'Arca D, Brausi M, Bettuzzi S, Corti A: The chemopreventive action of catechins in the TRAMP mouse model of prostate carcinogenesis is accompanied by clusterin over-expression. Carcinogenesis. 2004 Nov;25(11):2217-24. Epub 2004 Sep 9. Pubmed: 15358631 Link_out
  15. Ichihashi M, Ahmed NU, Budiyanto A, Wu A, Bito T, Ueda M, Osawa T: Preventive effect of antioxidant on ultraviolet-induced skin cancer in mice. J Dermatol Sci. 2000 Mar;23 Suppl 1:S45-50. Pubmed: 10764992 Link_out
  16. Dvorakova K, Dorr RT, Valcic S, Timmermann B, Alberts DS: Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin. Cancer Chemother Pharmacol. 1999;43(4):331-5. Pubmed: 10071985 Link_out
  17. Neuhaus T, Voit S, Lill G, Vetter H, Schror K, Weber AA: Platelet aggregation induced by the C-terminal peptide of thrombospondin-1 (4N1-1) is inhibited by epigallocatechin gallate but not by prostaglandin E1. Platelets. 2004 Nov;15(7):455-7. Pubmed: 15745318 Link_out
  18. Chen JJ, Ye ZQ, Koo MW: Growth inhibition and cell cycle arrest effects of epigallocatechin gallate in the NBT-II bladder tumour cell line. BJU Int. 2004 May;93(7):1082-6. Pubmed: 15142168 Link_out
  19. Kanadzu M, Lu Y, Morimoto K: Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes. Cancer Lett. 2006 Sep 28;241(2):250-5. Epub 2005 Nov 21. Pubmed: 16303244 Link_out
  20. Rezai-Zadeh K, Shytle D, Sun N, Mori T, Hou H, Jeanniton D, Ehrhart J, Townsend K, Zeng J, Morgan D, Hardy J, Town T, Tan J: Green tea epigallocatechin-3-gallate (EGCG) modulates amyloid precursor protein cleavage and reduces cerebral amyloidosis in Alzheimer transgenic mice. J Neurosci. 2005 Sep 21;25(38):8807-14. Pubmed: 16177050 Link_out