PhytoHub: Showing entry for (-)-Epicatechin

(-)-Epicatechin

Identification

PhytoHub ID

PHUB000262

Name

(-)-Epicatechin

Systematic Name

(−)-Epicatechin

Synonyms

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
3,5,7,3',4'-Pentahydroxyflavane
Epicatechol

CAS Number

490-46-0

Average Mass

290.271

Monoisotopic Mass

290.079038171

Chemical Formula

C₁₅H₁₄O₆

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

InChI Key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

InChI Identifier

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(O)C=C2O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 6.45e-01 g/l
LogS (ALOGPS): -2.65
LogP (ALOGPS): 1.02
Hydrogen Acceptors: 6
Hydrogen Donors: 5
Rotatable Bond Count: 1
Polar Surface Area: 110.38000000000001
Refractivity: 73.99970000000002
Polarizability: 28.70641069763134
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -3.2897193322428566
pKa (strongest acidic): 9.004573813837975
Number of Rings: 3
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavanols

Taxonomy as Metabolite

Metabolite Family: (Poly)phenol metabolites
Metabolite Class: Flavonoid metabolites
Metabolite Sub-class: Flavanols (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Procyanidin dimer B2	Polyphenols	Flavonoids	Flavanols	Show Food Phytochemical
(-)-Epicatechin	Polyphenols	Flavonoids	Flavanols	Show Food Phytochemical
Black tea Flavan-3-ols	Polyphenols	Flavonoids	Flavanols	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Flavans
Direct Parent Name: Catechins
Alternative Parent Names: ["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "3-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Benzene and substituted derivatives", "Catechols", "Hydrocarbon derivatives", "Oxacyclic compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations: ["Condensed tannins (Proanthocyanidins)", "Flavan 3-ols", "Flavans, Flavanols and Leucoanthocyanidins", "catechin", "polyphenol"]
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "3-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Catechin", "Catechol", "Chromane", "Ether", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Polyol", "Secondary alcohol"]

Spectra from Online Resources

Record ID	Source	Description	View
BML00626	MassBank	LC-ESI-QTOF Spectrum - 10 ev, unspecified	View Spectra
BML00630	MassBank	LC-ESI-QTOF Spectrum - 20 ev, unspecified	View Spectra
BML00634	MassBank	LC-ESI-QTOF Spectrum - 40 ev, unspecified	View Spectra
BML80050	MassBank	LC-ESI-QTOF Spectrum - -, unspecified	View Spectra
BML80051	MassBank	LC-ESI-QTOF Spectrum - -, unspecified	View Spectra
CE000088	MassBank	LC-ESI-ITFT Spectrum - 35eV, unspecified	View Spectra
CE000089	MassBank	LC-ESI-ITFT Spectrum - 45eV, unspecified	View Spectra
CE000090	MassBank	LC-ESI-ITFT Spectrum - 55eV, unspecified	View Spectra
CE000091	MassBank	LC-ESI-ITFT Spectrum - 70eV, unspecified	View Spectra
CE000092	MassBank	LC-ESI-ITFT Spectrum - -, unspecified	View Spectra
FIO00067	MassBank	LC-ESI-QTOF Spectrum - 10 eV, unspecified	View Spectra
FIO00068	MassBank	LC-ESI-QTOF Spectrum - 20 eV, unspecified	View Spectra
FIO00069	MassBank	LC-ESI-QTOF Spectrum - 30 eV, unspecified	View Spectra
FIO00070	MassBank	LC-ESI-QTOF Spectrum - 40 eV, unspecified	View Spectra
FIO00071	MassBank	LC-ESI-QTOF Spectrum - 50 eV, unspecified	View Spectra
FIO00072	MassBank	LC-ESI-QTOF Spectrum - 10 eV, unspecified	View Spectra
FIO00073	MassBank	LC-ESI-QTOF Spectrum - 20 eV, unspecified	View Spectra
FIO00074	MassBank	LC-ESI-QTOF Spectrum - 30 eV, unspecified	View Spectra
FIO00075	MassBank	LC-ESI-QTOF Spectrum - 40 eV, unspecified	View Spectra
FIO00076	MassBank	LC-ESI-QTOF Spectrum - 50 eV, unspecified	View Spectra
OUF00223	MassBank	GC-EI-TOF Spectrum - -, unspecified	View Spectra
PB001329	MassBank	LC-ESI-QTOF Spectrum - 15 eV, unspecified	View Spectra
PB001330	MassBank	LC-ESI-QTOF Spectrum - 25 eV, unspecified	View Spectra
PB001331	MassBank	LC-ESI-QTOF Spectrum - 40 eV, unspecified	View Spectra
PB001332	MassBank	LC-ESI-QTOF Spectrum - 55 eV, unspecified	View Spectra
PB001337	MassBank	LC-ESI-QTOF Spectrum - 15 eV, unspecified	View Spectra
PB001338	MassBank	LC-ESI-QTOF Spectrum - 25 eV, unspecified	View Spectra
PB001339	MassBank	LC-ESI-QTOF Spectrum - 40 eV, unspecified	View Spectra
PB001340	MassBank	LC-ESI-QTOF Spectrum - 55 eV, unspecified	View Spectra
PB002429	MassBank	LC-ESI-QTOF Spectrum - 15 eV, unspecified	View Spectra
PB002430	MassBank	LC-ESI-QTOF Spectrum - 25 eV, unspecified	View Spectra
PB002431	MassBank	LC-ESI-QTOF Spectrum - 40 eV, unspecified	View Spectra
PB002432	MassBank	LC-ESI-QTOF Spectrum - 55 eV, unspecified	View Spectra
PB006281	MassBank	LC-ESI-QTOF Spectrum - 10 eV, unspecified	View Spectra
PB006301	MassBank	LC-ESI-QTOF Spectrum - 15 eV, unspecified	View Spectra
PB006302	MassBank	LC-ESI-QTOF Spectrum - 20 eV, unspecified	View Spectra
PR100262	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100263	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100264	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100687	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100688	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra
PR100689	MassBank	LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified	View Spectra

Food Sources

Name	Group
Almond	Nuts	Publications	Show
Apple	Fruit, Pomes	Publications	Show
Apple cider	Beverages, Alcoholic	Publications	Show
Apple juice	Beverages, Non-alcoholic	Publications	Show
Apricot	Fruit, Drupes	Publications	Show
Beer	Beverages, Alcoholic	Publications	Show
Black tea	Teas and herbal teas	Publications	Show
Blackberry	Fruit, Berries	Publications	Show
Broad bean	Pulses and beans	Publications	Show
Chocolate	Cocoa and cocoa products	Publications	Show
Cider	Beverages, Alcoholic	Publications	Show
Cocoa	Cocoa and cocoa products	Publications	Show
Cocoa bean	Cocoa and cocoa products	Publications	Show
Cocoa powder	Cocoa and cocoa products	Publications	Show
Common chokecherry	Fruit, Drupes	Publications	Show
Common walnut	Nuts	Publications	Show
European cranberry	Fruit, Berries	Publications	Show
European plum	Fruit, Drupes	Publications	Show
Grape	Fruit, Berries	Publications	Show
Green tea	Teas and herbal teas		Show
Peach	Fruit, Drupes	Publications	Show
Pear	Fruit, Pomes	Publications	Show
Pomegranate	Fruit, Tropical fruits	Publications	Show
Strawberry	Fruit, Berries	Publications	Show
Sweet cherry	Fruit, Drupes	Publications	Show
Tea	Teas and herbal teas	Publications	Show

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
(-)-Epicatechin	Almond	Nuts	Publications	Show
Procyanidin dimer B2	Apple	Fruit, Pomes	Publications	Show
(-)-Epicatechin	Apple	Fruit, Pomes	Publications	Show
Procyanidin dimer B2	Apple cider	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Apple cider	Beverages, Alcoholic	Publications	Show
Procyanidin dimer B2	Apple juice	Beverages, Non-alcoholic	Publications	Show
(-)-Epicatechin	Apple juice	Beverages, Non-alcoholic	Publications	Show
Procyanidin dimer B2	Apricot	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Apricot	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Beer	Beverages, Alcoholic	Publications	Show
Procyanidin dimer B2	Black tea	Teas and herbal teas	Publications	Show
(-)-Epicatechin	Black tea	Teas and herbal teas	Publications	Show
Procyanidin dimer B2	Blackberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	Blackberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	Broad bean	Pulses and beans	Publications	Show
(-)-Epicatechin	Chocolate	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cider	Beverages, Alcoholic	Publications	Show
Procyanidin dimer B2	Cocoa	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cocoa	Cocoa and cocoa products	Publications	Show
Procyanidin dimer B2	Cocoa bean	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cocoa bean	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cocoa powder	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Common chokecherry	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Common walnut	Nuts	Publications	Show
(-)-Epicatechin	European cranberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	European plum	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Grape	Fruit, Berries	Publications	Show
Procyanidin dimer B2	Green tea	Teas and herbal teas	Publications	Show
(-)-Epicatechin	Green tea	Teas and herbal teas		Show
(-)-Epicatechin	Peach	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Pear	Fruit, Pomes	Publications	Show
(-)-Epicatechin	Pomegranate	Fruit, Tropical fruits	Publications	Show
(-)-Epicatechin	Strawberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	Sweet cherry	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Tea	Teas and herbal teas	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
(-)-Epicatechin	(-)-Epicatechin	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₄O₆	290.079038171	Detailed Intervention Studies
(-)-Epicatechin	4'-Hydroxyphenylacetic acid	human	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₈H₈O₃	152.047344118		Publications
(-)-Epicatechin	(-)-Epicatechin 3'-O-glucuronide	human	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin 3'-O-sulfate	human	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₄O₉S	370.035853205	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin 4'-O-glucuronide	human	plasma, urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin 4'-O-sulfate	human	plasma (minor), urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₄O₉S	370.035853205	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin 5-O-sulfate	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₄O₉S	370.035853205	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin 7-O-glucuronide	human rat	plasma, urine (major)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin glucuronide	human	plasma	Not Available	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.3989068		Publications
(-)-Epicatechin	(-)-Epicatechin sulfoglucuronide	human	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₅S	546.4612115		Publications
(-)-Epicatechin	(Epi)catechin O-glucuronide	human	ileal fluid, plasma, urine	Not Available	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.3989068		Publications
(-)-Epicatechin	(Epi)catechin O-sulfate	human	ileal fluid, plasma, urine	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₄O₉S	370.335352		Publications
(-)-Epicatechin	1-(3',4'-Dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₆O₆	292.094688235		Publications
(-)-Epicatechin	1-(Hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₆O₅	276.2896941		Publications
(-)-Epicatechin	3-(3',4'-Dihydroxyphenyl)propionic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₁₀O₄	182.057908802		Publications
(-)-Epicatechin	3-(3'-Hydroxyphenyl)propionic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₁₀O₃	166.062994182		Publications
(-)-Epicatechin	3'-Hydroxyphenylacetic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₈H₈O₃	152.047344118		Publications
(-)-Epicatechin	3'-O-Methyl-(-)-epicatechin 4'-O-sulfate	human	plasma, urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
(-)-Epicatechin	3'-O-Methyl-(-)-epicatechin 5-O-sulfate	human rat	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
(-)-Epicatechin	3'-O-Methyl-(-)-epicatechin 7-O-sulfate	human	plasma, urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
(-)-Epicatechin	3'-O-Methyl-(-)-epicatechin glucuronide	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.4258956		Publications
(-)-Epicatechin	3'-O-Methyl(epi)catechin O-sulfate	human	ileal fluid, plasma, urine	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.3623408		Publications
(-)-Epicatechin	4'-O-Methyl-(-)-epicatechin 5-O-sulfate	human	plasma (minor), urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
(-)-Epicatechin	4'-O-Methyl-(-)-epicatechin 7-O-sulfate	human	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
(-)-Epicatechin	4'-O-Methyl-(-)-epicatechin glucuronide	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.4258956	Detailed Intervention Studies	Publications
(-)-Epicatechin	4'-O-methyl(epi)catechin O-sulfate	human	ileal fluid, plasma, urine	Not Available	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.3623408		Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	in vitro (human) rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866		Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)valeric acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₄O₄	210.089208931		Publications
(-)-Epicatechin	5-(3'-hydroxyphenyl)valeric acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₄O₃	194.094294311		Publications
(-)-Epicatechin	Methyl-(-)-epicatechin sulfate	human	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₁₆H₁₆O₉S	384.3623408		Publications
(-)-Epicatechin	Methyl-(-)-epicatechin sulfoglucuronide	human	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₅S	560.4882003		Publications
(-)-Epicatechin	Phenylacetic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₈H₈O₂	136.052429498		Publications
(-)-Epicatechin	3-Hydroxyhippuric acid	human	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₉NO₄	195.053157774	Detailed Intervention Studies	Publications
(-)-Epicatechin	Hippuric acid	human rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₉NO₃	179.058243154	Detailed Intervention Studies	Publications
(-)-Epicatechin	5-(3'-Hydroxyphenyl)-gamma-valerolactone	in vitro (human)	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₁H₁₂O₃	192.078644246		Publications
(-)-Epicatechin	3-(3'-Hydroxyphenyl)hydracrylic acid	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₁₀O₄	182.057908802	Detailed Intervention Studies
(-)-Epicatechin	(-)-Epicatechin-5-O-glucuronide	human rat	plasma (minor), urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.111126148		Publications
(-)-Epicatechin	3'-O-Methoxy-(-)-epicatechin-5-O-glucuronide	human rat	plasma, urine	host metabolism	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.126776213		Publications
(-)-Epicatechin	5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid -4'-O-glucuronide	rat	plasma, urine	host metabolism	Not Available	Not Available	Not Available	C₁₇H₂₂O₁₁	402.116211528	Detailed Intervention Studies	Publications
(-)-Epicatechin	(-)-Epicatechin-7-O-glucuronide	human	urine	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₂O₁₂	466.111126148		Publications
(-)-Epicatechin	3'-O-Methyl-epicatechin	rat	urine	host metabolism	Not Available	Not Available	Not Available	C₁₆H₁₆O₆	304.094688235		Publications
(-)-Epicatechin	4-hydroxy-5-(3'-methoxyphenyl)valeric acid-4'-glucuronide	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₈H₂₄O₁₁	416.131861593		Publications
(-)-Epicatechin	5-(3'-Hydroxyphenyl)-gamma-hydroxyvaleric acid	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₄O₄	210.089208931		Publications
(-)-Epicatechin	5-(Phenyl)-gamma-hydroxyvaleric acid-3'-sulfate	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₃O₇S	289.038747513		Publications
(-)-Epicatechin	5-(Phenyl)-gamma-valerolactone-3'-sulfate	human rat	plasma, urine	host-gut microbiota co-metabolite	8h-12h	50-200 nmol/L	<1%	C₁₁H₁₁O₆S	271.028182828	Detailed Intervention Studies	Publications
(-)-Epicatechin	4-Hydroxybenzoic acid -3-sulfate	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₇H₅O₇S	232.976147255		Publications
(-)-Epicatechin	3-(4'-Hydroxyphenyl)propionic acid-3'-sulfate	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₉O₇S	261.007447384		Publications
(-)-Epicatechin	5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-beta-D-glucuronide	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₇H₂₀O₁₀	384.105646844		Publications
(-)-Epicatechin	5-(4'-hydroxyphenyl)-gamma-valerolactone-3'-sulfate	rat	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₁O₇S	287.023097448	Detailed Intervention Studies	Publications
(-)-Epicatechin	5-(4’-hydroxyphenyl)-gamma-valerolactone	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%	C₁₁H₁₂O₃	192.078644246		Publications
(-)-Epicatechin	3'-Methyl-epicatechin-7-O-glucuronide	human	Not Available	host metabolism	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.126776213		Publications
(-)-Epicatechin	4-hydroxy-5-(4'-hydroxyphenyl)valeric acid-3'-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₁H₁₄O₈S	306.040938585	Detailed Intervention Studies	Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-γ-valerolactone	human	plasma, urine	gut microbiota metabolite	5h-8h	<20 nmol/L	<1%				Publications
(-)-Epicatechin	5-(3'-hydroxyphenyl)-γ-valerolactone-4'-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%	C₁₁H₁₂O₇S	288.0303739	Detailed Intervention Studies	Publications
(-)-Epicatechin	5-(4′-Hydroxyphenyl)-γ-valerolactone-3′-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	0.5-2µmol/L	5-10%	C₁₇H₂₀O₁₀	384.105646844	Detailed Intervention Studies	Publications
(-)-Epicatechin	(−)-Epicatechin-7-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₄O₉S	370.035853205	Detailed Intervention Studies
(-)-Epicatechin	3′-Methoxy-(−)-epicatechin-7-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.126776213	Detailed Intervention Studies
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-sulfate-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%			Detailed Intervention Studies	Publications
(-)-Epicatechin	Dihydroxyphenylacetic acid-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available			Detailed Intervention Studies
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3′,5′-disulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	10-30%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4',5'-disulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	10-30%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-methoxy-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	5-(Dihydroxyphenyl)-γ-valerolactone-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%				Publications
(-)-Epicatechin	5-(Dihydroxyphenyl)-γ-valerolactone-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	5-10%				Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-methoxy-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	5-10%				Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	30-50%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-methoxy-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4′-sulfate	human	plasma	host-gut microbiota co-metabolite	1h-3h	<20 nmol/L	Not Available				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3′-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	8h-12h	50-200 nmol/L	<1%				Publications
(-)-Epicatechin	5-(5′-Hydroxyphenyl)-γ-valerolactone-3′-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	5-(5′-Hydroxyphenyl)-γ-valerolactone-3′-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4′-methoxy-3′-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3'-methoxy-4'-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	4-Hydroxy-5-(phenyl)valeric acid-3'-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₁H₁₄O₇S	290.046023965	Detailed Intervention Studies
(-)-Epicatechin	3'-Methoxy-(−)-epicatechin-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available			Detailed Intervention Studies
(-)-Epicatechin	5-(3′-Hydroxyphenyl)-γ-valerolactone-4′-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	200-500 nmol/L	1-5%				Publications
(-)-Epicatechin	5-(3′,5′-Dihydroxyphenyl)-γ-valerolactone	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	Methoxy-(−)-epicatechin-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available			Detailed Intervention Studies
(-)-Epicatechin	4-Hydroxy-5-(4'-hydroxyphenyl)valeric acid-3'-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₇H₂₂O₁₁	402.116211528		Publications
(-)-Epicatechin	5-(Phenyl)-valeric acid-sulfate-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	<20 nmol/L	<1%				Publications
(-)-Epicatechin	4-Hydroxy-5-(phenyl)valeric acid-methoxy-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%				Publications
(-)-Epicatechin	3′-Methoxy-(−)-epicatechin-5-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.126776213	Detailed Intervention Studies
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%				Publications
(-)-Epicatechin	4′-methoxy-(−)-epicatechin-7-β-D-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₂H₂₄O₁₂	480.126776213	Detailed Intervention Studies
Procyanidin dimer B2	(-)-Epicatechin	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₅H₁₄O₆	290.079038171		Publications
Black tea Flavan-3-ols	(-)-Epicatechin	human	plasma, urine	unchanged	1h-3h	50-200 nmol/L	5-10%	C₁₅H₁₄O₆	290.079038171		Publications

Inter-Individual Variations in Metabolism

Food Phytochemical	Metabolite	Effect	Value
(-)-Epicatechin	5-(Phenyl)-gamma-valerolactone-3'-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(4’-hydroxyphenyl)-gamma-valerolactone	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	4-hydroxy-5-(4'-hydroxyphenyl)valeric acid-3'-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-γ-valerolactone	Genotype	Discordant	Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-γ-valerolactone	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-γ-valerolactone	Smoking	Effect, clusters	Publications
(-)-Epicatechin	5-(3'-hydroxyphenyl)-γ-valerolactone-4'-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(4′-Hydroxyphenyl)-γ-valerolactone-3′-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-sulfate-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3′,5′-disulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4',5'-disulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-methoxy-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Dihydroxyphenyl)-γ-valerolactone-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Dihydroxyphenyl)-γ-valerolactone-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-methoxy-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Hydroxyphenyl)-γ-valerolactone-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-methoxy-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4′-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3′-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(5′-Hydroxyphenyl)-γ-valerolactone-3′-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(5′-Hydroxyphenyl)-γ-valerolactone-3′-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-4′-methoxy-3′-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-3'-methoxy-4'-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(3′-Hydroxyphenyl)-γ-valerolactone-4′-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(3′,5′-Dihydroxyphenyl)-γ-valerolactone	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	4-Hydroxy-5-(4'-hydroxyphenyl)valeric acid-3'-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-valeric acid-sulfate-glucuronide	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	4-Hydroxy-5-(phenyl)valeric acid-methoxy-sulfate	Microbiota	Effect, clusters	Publications
(-)-Epicatechin	5-(Phenyl)-γ-valerolactone-sulfate	Microbiota	Effect, clusters	Publications
Black tea Flavan-3-ols	(-)-Epicatechin	Genotype	Discordant	Publications
Black tea Flavan-3-ols	(-)-Epicatechin	Smoking	Effect, clusters	Publications

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