Record Information
Version1.0
Creation date2010-04-08 22:13:15 UTC
Update date2018-01-23 19:53:47 UTC
Primary IDFDB017702
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpigallocatechin 3-gallate
DescriptionPresent in black tea and green tea (Thea sinensis) 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. Epigallocatechin 3-gallate is found in many foods, some of which are broad bean, common bean, strawberry, and common walnut.
CAS Number989-51-5
Structure
Thumb
Synonyms
SynonymSource
(-)-Epigallocatechin-3-O-gallateChEBI
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoateChEBI
EGCGChEBI
Epigallocatechin 3-gallateChEBI
(-)-Epigallocatechin-3-O-gallic acidGenerator
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoic acidGenerator
Epigallocatechin 3-gallic acidGenerator
Epigallocatechin gallic acidGenerator
(-)-Epigallocatechin gallatHMDB
(-)-Epigallocatechin gallateHMDB
(-)-Epigallocatechol gallateHMDB
(-)-Epigallocatehin gallateHMDB
Catechin deriv.HMDB
Epigallocatcchin gallateHMDB
EpigallocateHMDB
Epigallocic acidHMDB
Galloyl-L-epigallocatecholHMDB
Tea catechinHMDB
Epigallo-catechin gallateHMDB
Epigallocatechin-3-gallateHMDB
SunphenonHMDB
EGCG CPDHMDB
Epigallocatechin-3-O-gallateHMDB
(-)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallatebiospider
(-)-EGCGbiospider
(-)-Epigallocatechin 3-gallatemanual
(-)-Epigallocatechin 3-O-gallatemanual
3-O-Galloylepigallocatechindb_source
Epigallocatechin 3-monogallatebiospider
Epigallocatechin gallatebiospider
L-Epigallocatechin gallatebiospider
Teatannin IIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP2.38ALOGPS
logP3.08ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.75 m³·mol⁻¹ChemAxon
Polarizability43.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H18O11
IUPAC name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=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-/m0/s1
InChI KeyWMBWREPUVVBILR-RXVVDRJESA-N
Isomeric SMILESOC1=CC2=C(C[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1
Average Molecular Weight458.3717
Monoisotopic Molecular Weight458.084911418
Classification
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
  • Epigallocatechin
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-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
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.65%; H 3.96%; O 38.39%DFC
Melting PointMp 245-247°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -179 (c, 0.3 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug0-0930000000-f01263ac8498e09a9b96View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-1192005000-c1fb4fee1e85d6928c34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0301900000-306bcb88a9db3b631447View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00or-0900000000-2209ff009c5d9cffaf40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0aor-0000900008-24e0bb519bd4a4f909f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0912000000-3adc2bfa8656374fadffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0900000000-421d0afdbaa8c277f57aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0911000000-8cd4fb88571a263c38abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0301900000-306bcb88a9db3b631447View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00or-0900000000-2209ff009c5d9cffaf40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0aor-0000900008-24e0bb519bd4a4f909f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0912000000-3adc2bfa8656374fadffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0900000000-421d0afdbaa8c277f57aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0911000000-8cd4fb88571a263c38abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0910000000-3ca87cd7e5536628266aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0159-0917000000-0d7d5d2e8b3cd65a6134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0159-0917000000-b1f0fb994ee815d3bc77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-d3719d6cc341aafdd5caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0901000000-bbef161918123e6de6a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0691000000-bf8635f20994642ca769View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0690000000-46717d45926c7c5d1a6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920500000-a974f0f3117ff4b93e42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0910100000-a2be3929b160816f337aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-c4f287a63df487615180View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0301900000-4bd59275b184970a157fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0916400000-8e2c614db7634a27ffddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-236dc720968cdbf03811View in MoNA
ChemSpider ID58575
ChEMBL IDCHEMBL297453
KEGG Compound IDC09731
Pubchem Compound ID65064
Pubchem Substance IDNot Available
ChEBI ID4806
Phenol-Explorer ID129
DrugBank IDNot Available
HMDB IDHMDB03153
CRC / DFC (Dictionary of Food Compounds) IDKZF28-J:KZF33-H
EAFUS IDNot Available
Dr. Duke IDEPIGALLOCATECHIN-3-GALLATE|(-)-EPIGALLOCATECHIN-3-GALLATE|(-)-EPIGALLOCATECHIN-GALLATE|(-)-EPIGALLOCATECHOL-GALLATE|EPIGALLOCATECHOL-GALLATE|(-)-EPIGALLOCATECHIN-3-O-GALLATE|EPIGALLOCATECHIN-3-O-GALLATE|EPIGALLOCATECHIN-GALLATE
BIGG IDNot Available
KNApSAcK IDC00000958
HET IDEGG
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEpigallocatechin gallate
Phenol-Explorer Metabolite ID129
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
acetyl-CoA-carboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.DUKE
anti mutagenicDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
anti proliferantDUKE
anti prostat adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti radicularDUKE
anti retinopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
catechol O-methyltransferase inhibitor48406 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
glucosyl-transferase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
GPTase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
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
methyl-guanidine inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
mitogen52290 A chemical substance that encourages a cell to commence cell division, triggering mitosis.DUKE
nephroprotective76595 Any protective agent that is able to prevent damage to the kidney.DUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
reverse transcriptase inhibitor59897 An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need to reproduce.DUKE
thermogenicDUKE
urokinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).