PhytoHub: Showing entry for 3'-O-Methyl-(-)-epicatechin 5-O-sulfate

3'-O-Methyl-(-)-epicatechin 5-O-sulfate

Identification

PhytoHub ID

PHUB001050

Name

3'-O-Methyl-(-)-epicatechin 5-O-sulfate

Systematic Name

3'-Methoxy-(−)-epicatechin-5-sulfate

Synonyms

Not Available

CAS Number

Not Available

Average Mass

384.36

Monoisotopic Mass

384.051503269

Chemical Formula

C₁₆H₁₆O₉S

IUPAC Name

[(2R,3R)-3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-5-yl]oxidanesulfonic acid

InChI Key

ZFUHNDPCTCXKQO-MLGOLLRUSA-N

InChI Identifier

InChI=1S/C16H16O9S/c1-23-15-4-8(2-3-11(15)18)16-12(19)7-10-13(24-16)5-9(17)6-14(10)25-26(20,21)22/h2-6,12,16-19H,7H2,1H3,(H,20,21,22)/t12-,16-/m1/s1

SMILES

[H][C@@]1(O)CC2=C(O[C@]1([H])C1=CC(OC)=C(O)C=C1)C=C(O)C=C2OS(O)(=O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.03e+00 g/l
LogS (ALOGPS): -2.57
LogP (ALOGPS): 0.06
Hydrogen Acceptors: 8
Hydrogen Donors: 4
Rotatable Bond Count: 4
Polar Surface Area: 142.75
Refractivity: 88.4738
Polarizability: 35.92499976323155
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -3.3097578068921245
pKa (strongest acidic): -2.2998193150240245
Number of Rings: 3
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 71579207

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

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", "3'-O-methylated flavonoids", "3-hydroxyflavonoids", "4'-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Anisoles", "Arylsulfates", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Organic oxides", "Oxacyclic compounds", "Phenoxy compounds", "Secondary alcohols", "Sulfuric acid monoesters"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "3-hydroxyflavonoid", "3p-methoxyflavonoid-skeleton", "4'-hydroxyflavonoid", "7-hydroxyflavonoid", "Alcohol", "Alkyl aryl ether", "Anisole", "Aromatic heteropolycyclic compound", "Arylsulfate", "Benzenoid", "Benzopyran", "Catechin", "Chromane", "Ether", "Hydrocarbon derivative", "Hydroxyflavonoid", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organic sulfuric acid or derivatives", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Phenol ether", "Phenoxy compound", "Secondary alcohol", "Sulfate-ester", "Sulfuric acid ester", "Sulfuric acid monoester"]

Spectra from Online Resources

No spectra information available

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		3'-O-Methyl-(-)-epicatechin 5-O-sulfate	human rat	plasma, plasma (major), urine, urine (major)	host metabolism	1h-3h	50-200 nmol/L	1-5%	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications
	Cocoa Flavan-3-ols		3'-O-Methyl-(-)-epicatechin 5-O-sulfate	human	plasma	host metabolism	1h-3h	50-200 nmol/L	Not Available	C₁₆H₁₆O₉S	384.051503269	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	Cocoa Flavan-3-ols		3'-O-Methyl-(-)-epicatechin 5-O-sulfate	Age	Discordant	Publications

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Showing entry for 3'-O-Methyl-(-)-epicatechin 5-O-sulfate