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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 17:21:01 UTC
Update Date2021-09-23 17:21:01 UTC
HMDB IDHMDB0302380
Secondary Accession NumbersNone
Metabolite Identification
Common Nameent-Epigallocatechin 3-gallate
DescriptionEnt-epigallocatechin 3-gallate is a member of the class of compounds known as catechin gallates. Catechin gallates are organic compounds containing a gallate moiety glycosidically linked to a catechin. Ent-epigallocatechin 3-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-epigallocatechin 3-gallate can be found in tea, which makes ent-epigallocatechin 3-gallate a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
ent-Epigallocatechin 3-gallic acidGenerator
Chemical FormulaC22H18O11
Average Molecular Weight458.3717
Monoisotopic Molecular Weight458.084911418
IUPAC Name(2S,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2S,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC2=C(O)C=C(O)C=C2O[C@@]1([H])C1=CC(O)=C(O)C(O)=C1)OC(=O)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-/m0/s1
InChI KeyWMBWREPUVVBILR-RXVVDRJESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
Polarizability42.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+204.65632859911
AllCCS[M+H-H2O]+202.27632859911
AllCCS[M+Na]+207.46832859911
AllCCS[M+NH4]+206.84332859911
AllCCS[M-H]-201.03932859911
AllCCS[M+Na-2H]-200.94532859911
AllCCS[M+HCOO]-201.00232859911
DeepCCS[M+H]+203.00830932474
DeepCCS[M-H]-201.11230932474
DeepCCS[M-2H]-234.35330932474
DeepCCS[M+Na]+208.87730932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ent-Epigallocatechin 3-gallate,3TBDMS,isomer #24CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O)=C1O5037.7Semi standard non polar33892256
ent-Epigallocatechin 3-gallate,3TBDMS,isomer #24CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O)=C1O4597.0Standard non polar33892256
ent-Epigallocatechin 3-gallate,3TBDMS,isomer #24CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)=CC(O)=C1O5449.6Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 10V, Positive-QTOFsplash10-052r-0920500000-a974f0f3117ff4b93e422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 20V, Positive-QTOFsplash10-0fe0-0910100000-a2be3929b160816f337a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 40V, Positive-QTOFsplash10-0079-2900000000-c4f287a63df4876151802016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 10V, Negative-QTOFsplash10-0a4i-0301900000-4bd59275b184970a157f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 20V, Negative-QTOFsplash10-066r-0916400000-8e2c614db7634a27ffdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 40V, Negative-QTOFsplash10-00or-0900000000-236dc720968cdbf038112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 10V, Positive-QTOFsplash10-0a4r-0262900000-13b8794854ac956a81242021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 20V, Positive-QTOFsplash10-052r-0944400000-29d2ad1c7cd03d5a8c4e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 40V, Positive-QTOFsplash10-0uy0-0912000000-5c2a2bf8c6513a2a44322021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 10V, Negative-QTOFsplash10-0aor-0902600000-2525680e976a7c94c3382021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 20V, Negative-QTOFsplash10-0gdr-0920100000-4918a492fc537262ef822021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epigallocatechin 3-gallate 40V, Negative-QTOFsplash10-05p9-3905100000-1a0255528a320863806f2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017702
KNApSAcK IDNot Available
Chemspider ID2103000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2824823
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available