ent-Gallocatechin 3-gallate (CHEM022884)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:43:05 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022884
Identification
Common Nameent-Gallocatechin 3-gallate
ClassSmall Molecule
DescriptionA gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-gallocatechin. A natural product found in found in green tea.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Gallocatechin-3-O-gallateChEBI
(-)-Gallocatechol gallateChEBI
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)ChEBI
(2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoateChEBI
(-)-Gallocatechin-3-O-gallic acidGenerator
(-)-Gallocatechol gallic acidGenerator
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoic acid)Generator
(2S,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
(-)-Gallocatechin gallic acidGenerator
Gallocatechin gallateMeSH
Gallocatechin-3-gallateMeSH
ent-Gallocatechin 3-gallic acidGenerator
Chemical FormulaC22H18O11
Average Molecular Mass458.372 g/mol
Monoisotopic Mass458.085 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Namegallocatechin gallate
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
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+/m1/s1
InChI KeyWMBWREPUVVBILR-NQIIRXRSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Phenolic glycoside
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • Butyrophenone
  • Glycosyl compound
  • O-glycosyl compound
  • Phenylketone
  • Benzoyl
  • Phenoxy compound
  • Catechol
  • Phenol ether
  • Resorcinol
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability42.81 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 32V, positivesplash10-000i-0190000000-7e3ba3906a46eece7bf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 32V, positivesplash10-000i-0490000000-4b05c52a99e0c4b78928Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920500000-a974f0f3117ff4b93e42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0910100000-a2be3929b160816f337aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-c4f287a63df487615180Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0301900000-4bd59275b184970a157fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0916400000-8e2c614db7634a27ffddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-236dc720968cdbf03811Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4u-0161900000-93fcf1085dda87e2eef3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvr-0974800000-fe2b35b2b9c1b0d68fc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fs9-0925100000-97364265724fdd2727cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0003900000-8f91dc75ff31c110b853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kw0-0911300000-cfe0a1ddf5316282d1abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00vr-1914200000-6052bd4777f8f2b91366Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301673
FooDB IDFDB000095
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGallocatechin_gallate
Chemspider ID172662
ChEBI ID156271
PubChem Compound ID199472
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10929811
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20410646
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21212555
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22350287
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22619553
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=31215023
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=31376653