Record Information
Version1.0
Creation date2010-04-08 22:12:51 UTC
Update date2018-05-29 01:29:54 UTC
Primary IDFDB017114
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpicatechin 3-gallate
DescriptionIsolated from tea and numerous other plant subspecies inc. rhubarb and grapes. Epicatechin 3-gallate is found in many foods, some of which are cucumber, muskmelon, black raspberry, and cashew nut.
CAS Number1257-08-5
Structure
Thumb
Synonyms
SynonymSource
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallateChEBI
3-Gallate(-)-epicatecholChEBI
3-O-GalloylepicatechinChEBI
ECGChEBI
TeatanninChEBI
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallic acidGenerator
3-Gallic acid(-)-epicatecholGenerator
(-)-Epicatechin 3-O-gallic acidGenerator
(-)-Epicatechin gallateHMDB
(-)-Epicatechin-3-gallateHMDB
(-)-Epicatechin-3-O-gallateHMDB
Epicatechin gallateHMDB
Epicatechin gallate, (2R-cis)-isomerHMDB
Epicatechol, gallateHMDB
L-Epicatechin gallateHMDB
Epicatechin-3-O-gallateHMDB
Epicatechin-3-gallateHMDB
Epicatechin-3-galloyl esterHMDB
(-)-Epicatechin 3-gallatemanual
(-)-Epicatechin 3-O-gallatemanual
Epicatechin 3-gallatemanual
Epicatechol, 3-gallate, (-)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.55ALOGPS
logP3.38ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.76 m³·mol⁻¹ChemAxon
Polarizability41.64 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H18O10
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChI KeyLSHVYAFMTMFKBA-TZIWHRDSSA-N
Isomeric SMILESOC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1
Average Molecular Weight442.376
Monoisotopic Molecular Weight442.08999678
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
  • 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
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.73%; H 4.10%; O 36.17%DFC
Melting PointMp 257-258° (253°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -160.6 (c, 0.22 in Me2CO)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, Positivesplash10-0umi-0920000000-718b2102383cc9dc533eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004l-1490224000-de77e2646c7aba3a8defView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-ece704ccdb047a088d28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-d89b96c676e7c3398d8fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0170-0950000000-685c095616785cc82303View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0940200000-84b58b678cc59833a025View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-440ff7c7a589e1c058b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-8f606522637d9033c95fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0098500000-0c0b2ca06b9e49aa356bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0097500000-7a41879feecb968154e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-77ceea44aa3ce7f822f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-7f271696d73430ee7463View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-21da01e01ba7fa12d6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0920400000-e7005e91544f51f7efe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0910000000-a428a4e56e1884d5b86aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-d86fe441a677946b2205View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0310900000-98e9c41598a749627127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdl-0913300000-af1ea1d6588fca8f1f9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-60192713dbf412058de2View in MoNA
ChemSpider ID97034
ChEMBL IDCHEMBL36327
KEGG Compound IDNot Available
Pubchem Compound ID107905
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID128
DrugBank IDNot Available
HMDB IDHMDB37944
CRC / DFC (Dictionary of Food Compounds) IDCML31-M:KWF59-Y
EAFUS IDNot Available
Dr. Duke IDEPICATECHIN-GALLATE|(-)-EPICATECHIN-GALLATE|(-)-EPICATECHOL-GALLATE|1-EPICATECHIN-GALLATE|EPICATECHIN-3-O-GALLATE|EPICATECHOL-GALLATE|(-)-EPICATECHIN-3-O-GALLATE|(-)-EPICATECHIN-3-GALLATE|EPICATECHIN-3-GALLATE
BIGG IDNot Available
KNApSAcK IDC00008866
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID128
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
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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti mutagenicDUKE
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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.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
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
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
alpha-amylase inhibitor50627 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).CHEBI
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
MSDSNot Available
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).