precursor

Showing entry for (-)-Epicatechin 3-O-gallate

Identification

PhytoHub ID
PHUB000263
Name
(-)-Epicatechin 3-O-gallate
Systematic Name
(−)-Epicatechin-3-O-gallate
Synonyms
Not Available
CAS Number
1257-08-5
Average Mass
442.376
Monoisotopic Mass
442.08999678
Chemical Formula
C22H18O10
IUPAC Name
Not Available
InChI Key
LSHVYAFMTMFKBA-TZIWHRDSSA-N
InChI Identifier
InChI=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
SMILES
OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.43e-02 g/l
LogS (ALOGPS)
-4.00
LogP (ALOGPS)
2.55
Hydrogen Acceptors
Not Available
Hydrogen Donors
Not Available
Rotatable Bond Count
Not Available
Polar Surface Area
Not Available
Refractivity
Not Available
Polarizability
Not Available
Formal Charge
Not Available
Physiological Charge
Not Available
pKa (strongest basic)
Not Available
pKa (strongest acidic)
Not Available
Number of Rings
Not Available
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavan-3-ols

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavans
Direct Parent Name
Catechin gallates
Alternative Parent Names
["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Benzoyl derivatives", "Carboxylic acid esters", "Catechols", "Galloyl esters", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Oxacyclic compounds", "Polyols", "Pyrogallols and derivatives", "m-Hydroxybenzoic acid esters", "p-Hydroxybenzoic acid alkyl esters"]
External Descriptor Annotations
["Flavans, Flavanols and Leucoanthocyanidins", "catechin", "gallate ester", "polyphenol"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Benzenetriol", "Benzenoid", "Benzoate ester", "Benzoic acid or derivatives", "Benzopyran", "Benzoyl", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechin gallate", "Catechol", "Chromane", "Ether", "Gallic acid or derivatives", "Galloyl ester", "Hydrocarbon derivative", "Hydroxyflavonoid", "M-hydroxybenzoic acid ester", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "P-hydroxybenzoic acid alkyl ester", "P-hydroxybenzoic acid ester", "Phenol", "Polyol", "Pyrogallol derivative"]

Spectra from Phytohub

Spectrum TypeInstrument TypeTechnologyIon ModeCollision EnergyView
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: C[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(O)=C3)O2)C(O[Si](C)(C)C)=C1)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(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=C1O)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(C)(C)[Si](C)(C)OC1=CC([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)=CC=C1O)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(C)(C)[Si](C)(C)OC1=CC([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)=CC=C1O)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0EiNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: Semi standard non polar)PositiveNot AvailableView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQnegativeVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQnegativeVView Spectrum
LC-MS/MSNot Availableinstrument=Maxis II HD Q-TOF BrukernegativeVView Spectrum
LC-MS/MSNot Availableinstrument=Maxis II HD Q-TOF BrukernegativeVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSLinear Ion Trapinstrument=Thermo Finnigan LTQpositiveVView Spectrum
LC-MS/MSNot Availableinstrument=Maxis II HD Q-TOF BrukerpositiveVView Spectrum
LC-MS/MSNot AvailableNot AvailablePositive40VView Spectrum
LC-MS/MSNot AvailableNot AvailableNegative35VView Spectrum
LC-MS/MSNot AvailableNot AvailablePositive20VView Spectrum
LC-MS/MSNot AvailableNot AvailablePositive10VView Spectrum
LC-MS/MSNot AvailableNot AvailableNegative10VView Spectrum
LC-MS/MSNot AvailableNot AvailableNegative20VView Spectrum
LC-MS/MSNot AvailableNot AvailableNegative40VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive40VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative40VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-ID 4.0Negative10VView Spectrum

Food Sources

NameGroup
Black teaTeas and herbal teas PublicationsShow
Green teaTeas and herbal teas PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
(-)-Epicatechin 3-O-gallate (-)-Epicatechin 3-O-gallatehumanplasmahost metabolism1h-3h20-50 nmol/LNot AvailableC22H18O10442.08999678 Detailed Intervention Studies Publications
(-)-Epicatechin 3-O-gallate (Epi)catechin 3-O-gallate O-sulfatehumanileal fluid, plasmaNot AvailableNot AvailableNot AvailableNot AvailableC22H18O13S522.4417344 Publications
(-)-Epicatechin 3-O-gallate O-Methyl(epi)catechin-3-O-gallate O-sulfatehumanileal fluidNot AvailableNot AvailableNot AvailableNot AvailableC23H20O13S536.4687232 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
(-)-Epicatechin 3-O-gallate (-)-Epicatechin 3-O-gallateGenotypeEffect, clusters Publications
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