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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:11:37 UTC
Update Date2022-03-07 02:55:57 UTC
HMDB IDHMDB0038846
Secondary Accession Numbers
  • HMDB38846
Metabolite Identification
Common Name(-)-Epiafzelechin 3-gallate
Description(-)-Epiafzelechin 3-gallate, also known as epiafzelechin 3-O-gallic acid, belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4 (-)-Epiafzelechin 3-gallate is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make (-)-epiafzelechin 3-gallate a potential biomarker for the consumption of these foods (-)-Epiafzelechin 3-gallate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on (-)-Epiafzelechin 3-gallate.
Structure
Data?1563863268
Synonyms
ValueSource
(-)-Epiafzelechin 3-O-gallateChEBI
Epiafzelechin 3-O-gallateChEBI
(-)-Epiafzelechin 3-O-gallic acidGenerator
Epiafzelechin 3-O-gallic acidGenerator
(-)-Epiafzelechin 3-gallic acidGenerator
(-)-Epiafzelechin gallateChEMBL, HMDB
(-)-Epiafzelechin gallic acidGenerator, HMDB
3-Galloyl-(-)-epiafzelechinHMDB
(-)-Epiafzelechin 3-gallateChEBI
Chemical FormulaC22H18O9
Average Molecular Weight426.3729
Monoisotopic Molecular Weight426.095082174
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Nameepiafzelechin 3-O-gallate
CAS Registry Number108907-43-3
SMILES
OC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C2
InChI Identifier
InChI=1S/C22H18O9/c23-12-3-1-10(2-4-12)21-19(9-14-15(25)7-13(24)8-18(14)30-21)31-22(29)11-5-16(26)20(28)17(27)6-11/h1-8,19,21,23-28H,9H2/t19-,21-/m1/s1
InChI KeySDZPYNMXGUHFMZ-TZIWHRDSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavan-3-ols
Alternative Parents
Substituents
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
Water Solubility0.024 g/LALOGPS
logP2.74ALOGPS
logP3.68ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.78 m³·mol⁻¹ChemAxon
Polarizability41.25 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
DarkChem[M+H]+199.28831661259
DarkChem[M-H]-199.2631661259
DeepCCS[M+H]+190.05630932474
DeepCCS[M-H]-187.6630932474
DeepCCS[M-2H]-220.54430932474
DeepCCS[M+Na]+195.96830932474
AllCCS[M+H]+199.932859911
AllCCS[M+H-H2O]+197.332859911
AllCCS[M+NH4]+202.432859911
AllCCS[M+Na]+203.132859911
AllCCS[M-H]-196.132859911
AllCCS[M+Na-2H]-195.832859911
AllCCS[M+HCOO]-195.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-Epiafzelechin 3-gallateOC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C25920.4Standard polar33892256
(-)-Epiafzelechin 3-gallateOC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C24153.0Standard non polar33892256
(-)-Epiafzelechin 3-gallateOC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C24414.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Epiafzelechin 3-gallate,1TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14237.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TMS,isomer #2C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O4200.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TMS,isomer #3C[Si](C)(C)OC1=C(O)C=C(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)C=C1O4190.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TMS,isomer #4C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](C1=CC=C(O)C=C1)O24184.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TMS,isomer #5C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14230.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14088.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #10C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14095.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #11C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C14048.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14056.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C)=C2)C=C14108.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O)=C2)C=C14096.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #5C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(C=C(O)C=C3O[Si](C)(C)C)O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O4072.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #6C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14104.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #7C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C1O4117.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #8C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O[Si](C)(C)C4076.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TMS,isomer #9C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C1)[C@@H](C1=CC=C(O)C=C1)O24068.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C13897.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #10C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](C1=CC=C(O)C=C1)O23902.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #11C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C13925.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #12C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C13899.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #13C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C3971.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #14C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C13838.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C)=C2)C=C13881.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O)=C2)C=C13884.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C)=C2)C=C13898.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #5C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O)=C2)C=C13857.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C2)C=C13974.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #7C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13926.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #8C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C13866.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TMS,isomer #9C[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(C=C(O)C=C3O[Si](C)(C)C)O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C1O3930.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C)=C2)C=C13760.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #10C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](C1=CC=C(O)C=C1)O23850.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #11C[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C13843.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O)=C2)C=C13852.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C2)C=C13824.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13816.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #5C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C2)C=C13805.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13790.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #7C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13868.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #8C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C13788.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TMS,isomer #9C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C13773.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,5TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C2)C=C13833.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,5TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13819.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,5TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13823.2Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,5TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13806.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,5TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C13779.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,6TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C=C13819.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14546.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O4533.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)C=C1O4535.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](C1=CC=C(O)C=C1)O24502.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14522.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14677.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14632.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #11CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14616.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14641.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14723.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([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)=C2)C=C14721.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O4642.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14662.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1O4717.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O)=C1O[Si](C)(C)C(C)(C)C4656.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@@H](C1=CC=C(O)C=C1)O24619.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C14651.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C1=CC=C(O)C=C1)O24647.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14694.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14650.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4694.1Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14647.7Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14679.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C14723.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14664.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C14697.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14767.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC=C([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)C=C14705.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14622.9Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O[C@@H]2CC3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O[C@@H]2C2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1O4675.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14757.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C1=CC=C(O)C=C1)O24705.4Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #11CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)OC2=C14710.6Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C=C14832.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14826.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=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)C=C14780.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14801.3Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=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)C=C14754.0Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2OC(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C=C14766.8Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14753.5Semi standard non polar33892256
(-)-Epiafzelechin 3-gallate,4TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14704.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Epiafzelechin 3-gallate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-0930000000-49a61f43c54f5b8cd7542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Epiafzelechin 3-gallate GC-MS (3 TMS) - 70eV, Positivesplash10-0ufr-0900121000-d2ea5029d7ff2cf33f362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Epiafzelechin 3-gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Epiafzelechin 3-gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 10V, Positive-QTOFsplash10-002r-0920400000-26bc012ba94e75ded8f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 20V, Positive-QTOFsplash10-0fki-0910000000-9aaf820c6fcff2c0d7ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 40V, Positive-QTOFsplash10-00dr-3900000000-87d95cedf72475332b662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 10V, Negative-QTOFsplash10-004i-0310900000-5a0d5da96ff90679f69b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 20V, Negative-QTOFsplash10-00or-0951300000-e56c605bb0f7c08029a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 40V, Negative-QTOFsplash10-00or-1900000000-ebf59da24ada4ffef2342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 10V, Positive-QTOFsplash10-0a6r-0150900000-b1a03a175652e31d20432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 20V, Positive-QTOFsplash10-0kbr-0952300000-70aa7b9e2e90c768c2a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 40V, Positive-QTOFsplash10-0553-1942000000-15d94da7924a9f8adf172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 10V, Negative-QTOFsplash10-004i-0030900000-8ffa4234223e962af0262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 20V, Negative-QTOFsplash10-05r0-0933400000-484e49d715ff3b9f99d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Epiafzelechin 3-gallate 40V, Negative-QTOFsplash10-002u-3913100000-a363bf1373dc138b7f1e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB018281
KNApSAcK IDC00008864
Chemspider ID410660
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound467295
PDB IDNot Available
ChEBI ID136552
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 References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .