PhytoHub: Showing entry for (-)-Epicatechin 3'-O-glucuronide

(-)-Epicatechin 3'-O-glucuronide

Identification

PhytoHub ID

PHUB001029

Name

(-)-Epicatechin 3'-O-glucuronide

Systematic Name

(−)-Epicatechin-3'-glucuronide

Synonyms

Not Available

CAS Number

Not Available

Average Mass

466.395

Monoisotopic Mass

466.111126148

Chemical Formula

C₂₁H₂₂O₁₂

IUPAC Name

3,4,5-trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylic acid

InChI Key

VBSMBNMUYITMLB-IUODEOHRSA-N

InChI Identifier

InChI=1S/C21H22O12/c22-8-4-11(24)9-6-12(25)18(31-13(9)5-8)7-1-2-10(23)14(3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15?,16?,17?,18-,19?,21?/m1/s1

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(OC3OC(C(O)C(O)C3O)C(O)=O)=C1)C=C(O)C=C2O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 2.89e+00 g/l
LogS (ALOGPS): -2.21
LogP (ALOGPS): 0.08
Hydrogen Acceptors: 12
Hydrogen Donors: 8
Rotatable Bond Count: 4
Polar Surface Area: 206.59999999999997
Refractivity: 106.01149999999998
Polarizability: 43.65327109105406
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -3.6868279761800333
pKa (strongest acidic): 3.0064421603129543
Number of Rings: 4
Rule of Five: No
Bioavailability: No
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Flavonoid metabolites
Sub-class: Flavan-3-ols (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
(-)-Epicatechin	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Cocoa Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Green tea Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical

Spectra from Online Resources

No spectra information available

Spectra from Phytohub

Spectrum Type	Description	Splash Key	Deposition Date	View

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
(-)-Epicatechin	Almond	Nuts	Publications	Show
(-)-Epicatechin	Apple	Fruit, Pomes	Publications	Show
(-)-Epicatechin	Apple cider	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Apple juice	Beverages, Non-alcoholic	Publications	Show
(-)-Epicatechin	Apricot	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Beer	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Black tea	Teas and herbal teas	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
(-)-Epicatechin	Cocoa	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
(-)-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 3'-O-glucuronide	human	plasma, plasma (major), urine, urine (major)	host metabolism	1h-3h	200-500 nmol/L	1-5%	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications
Cocoa Flavan-3-ols	(-)-Epicatechin 3'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	200-500 nmol/L	<1%	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications
Green tea Flavan-3-ols	(-)-Epicatechin 3'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	20-50 nmol/L	<1%	C₂₁H₂₂O₁₂	466.111126148	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	Cocoa Flavan-3-ols		(-)-Epicatechin 3'-O-glucuronide	Age	Discordant	Publications

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Showing entry for (-)-Epicatechin 3'-O-glucuronide