metabolite

Showing entry for 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

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 PhytochemicalFamilyClassSub-class
(-)-EpicatechinPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Cocoa Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow 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 Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(80.96463989,0.9511611631);(98.97520458,0.5364954902);(125.0602545,1.122775379);(151.0395191,0.8119068544);(153.0551691,2.318021287);(161.0602545,0.75159211);(179.0708192,0.8408691955);(183.0657338,0.2970449562);(187.0065047,0.3534555098);(195.0657338,0.5761672018);(197.0813839,1.54172652);(203.0014193,5.117346093);(205.0170694,1.304398881);(212.9857693,0.3064012688);(218.9963339,14.65237682);(221.011984,0.7058931293);(223.0276341,0.6877888459);(228.9806839,0.3551460609);(230.9963339,0.494947971);(233.011984,0.3517562736);(269.0813839,0.650298191);(285.0762985,2.203130293);(287.0919486,3.971256491);(305.1025133,0.5766779148);(349.0381988,1.165383101);(353.0331134,0.8635344088);(355.0487634,0.7658361916);(367.0487634,6.737936579);(367.0487634,9.376296473);(369.028028,0.7814499567);(385.0593281,38.83092939)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(80.96463989,3.929095682);(109.0289544,1.269103116);(123.0446045,3.358919606);(125.0602545,2.030649477);(137.0602545,2.56744489);(139.0395191,9.195077214);(151.0395191,2.073947847);(153.0551691,5.257470453);(187.0065047,0.8627226816);(188.9857693,1.365891355);(197.0813839,0.9472486186);(203.0014193,4.188806878);(205.0170694,1.061630353);(218.9963339,20.35218487);(230.9963339,0.9486623426);(249.0068986,0.7370934296);(269.0813839,1.486586799);(275.0919486,1.341606627);(287.0919486,5.077683817);(287.0919486,5.200400081);(299.0555631,0.7325061183);(301.0712131,0.8194219604);(303.0868632,0.9139803337);(305.1025133,5.702114402);(349.0381988,2.224022168);(349.0381988,1.869251221);(353.0331134,0.7623938945);(355.0487634,1.484869333);(367.0487634,5.208655952);(367.0487634,2.489065417);(385.0593281,4.541493062)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(51.0234751,1.470273548);(53.03912516,2.173002792);(55.01838972,1.543925643);(80.96463989,2.841147505);(81.03403978,2.040014173);(93.03403978,3.366958446);(107.0496898,6.472275284);(109.0289544,1.749614366);(121.0289544,1.42248907);(123.0446045,8.294831922);(125.0602545,1.890359299);(133.0289544,1.890610589);(135.0446045,1.29817146);(137.0602545,8.004434002);(139.0395191,1.402956358);(139.0759046,1.872618211);(151.0395191,3.637392976);(153.0551691,3.634170756);(161.0602545,3.564269918);(174.9701192,2.532944655);(176.9857693,2.107545447);(179.0708192,1.419513087);(187.0065047,2.706491471);(203.0014193,15.68330114);(205.0170694,2.07082037);(212.9857693,1.769492004);(215.0014193,2.39726619);(217.0170694,1.289425403);(218.9963339,2.790420787);(228.9806839,4.298958215);(230.9963339,2.36430491)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(80.96463989,0.9161795074);(82.98028996,0.7835627216);(96.95955451,1.179508814);(107.0133043,0.3233544531);(123.0446045,2.908605494);(151.0395191,0.8437664427);(165.0551691,0.9373318559);(181.0500838,1.296127585);(186.9701192,1.107801191);(195.0657338,0.8036838423);(200.9857693,1.381855034);(204.9806839,0.3542445912);(216.9806839,5.056852779);(218.9963339,1.354966303);(258.9912486,0.9337109896);(281.0449984,0.3018650434);(283.0606485,0.4108874494);(285.0762985,1.206058376);(285.0762985,0.8581325104);(287.0555631,0.3054380637);(297.039913,0.6379055753);(299.0555631,0.4254159318);(301.0712131,0.2817520346);(303.0868632,3.619589037);(341.0331134,0.2819229705);(351.0174633,0.3247653564);(353.0331134,1.514832741);(365.0331134,2.357262569);(365.0331134,4.887655705);(367.0123779,0.8224730514);(383.0436781,61.58249198)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(80.96463989,1.091678544);(96.95955451,1.208089795);(107.0133043,2.763160216);(121.0289544,1.01100415);(123.0446045,2.781716413);(135.0446045,2.09901781);(137.023869,4.570968651);(147.0446045,1.27487838);(149.023869,0.8831604533);(151.0395191,2.502830166);(163.0395191,2.078131355);(165.0551691,12.31531574);(177.0551691,2.457331382);(186.9701192,2.170092388);(204.9806839,0.9972221442);(216.9806839,7.948855499);(247.0606485,1.109699223);(258.9912486,0.9180953742);(261.0762985,1.071984829);(271.0606485,0.9735307794);(285.0762985,1.407831195);(285.0762985,4.396756865);(287.0555631,7.510363241);(297.039913,1.372780221);(299.0555631,1.955497672);(301.0712131,2.736825876);(303.0868632,13.03610199);(339.0174633,1.020332839);(365.0331134,2.760910671);(367.0123779,3.098259158);(383.0436781,8.477576974)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(64.96972527,1.414264582);(80.96463989,6.413924613);(82.98028996,0.8822482307);(84.99594002,1.378101423);(107.0133043,17.09916052);(121.0289544,6.208120556);(123.0446045,3.609609221);(125.023869,3.64795042);(135.0446045,2.398664263);(137.023869,5.706106434);(141.0551691,0.9084987082);(149.023869,0.8401582774);(151.0395191,2.430122784);(162.9701192,1.30599356);(165.0551691,1.741277286);(170.9752046,1.190965037);(177.0551691,1.283147068);(179.0344337,2.652302678);(186.9701192,7.653100445);(188.9493838,1.039635208);(200.9857693,1.017232578);(204.9806839,10.55085225);(216.9806839,1.181396449);(259.0606485,2.444039856);(261.0762985,1.928297813);(271.0606485,1.111407748);(285.0762985,1.831682196);(287.0555631,6.514368888);(303.0868632,1.302519345);(339.0174633,0.9512965181);(365.0331134,1.363555046)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
(-)-EpicatechinAlmondNuts PublicationsShow
(-)-EpicatechinAppleFruit, Pomes PublicationsShow
(-)-EpicatechinApple ciderBeverages, Alcoholic PublicationsShow
(-)-EpicatechinApple juiceBeverages, Non-alcoholic PublicationsShow
(-)-EpicatechinApricotFruit, Drupes PublicationsShow
(-)-EpicatechinBeerBeverages, Alcoholic PublicationsShow
(-)-EpicatechinBlack teaTeas and herbal teas PublicationsShow
(-)-EpicatechinBlackberryFruit, Berries PublicationsShow
(-)-EpicatechinBroad beanPulses and beans PublicationsShow
(-)-EpicatechinChocolateCocoa and cocoa products PublicationsShow
(-)-EpicatechinCiderBeverages, Alcoholic PublicationsShow
(-)-EpicatechinCocoaCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa beanCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa powderCocoa and cocoa products PublicationsShow
(-)-EpicatechinCommon chokecherryFruit, Drupes PublicationsShow
(-)-EpicatechinCommon walnutNuts PublicationsShow
(-)-EpicatechinEuropean cranberryFruit, Berries PublicationsShow
(-)-EpicatechinEuropean plumFruit, Drupes PublicationsShow
(-)-EpicatechinGrapeFruit, Berries PublicationsShow
(-)-EpicatechinGreen teaTeas and herbal teasShow
(-)-EpicatechinPeachFruit, Drupes PublicationsShow
(-)-EpicatechinPearFruit, Pomes PublicationsShow
(-)-EpicatechinPomegranateFruit, Tropical fruits PublicationsShow
(-)-EpicatechinStrawberryFruit, Berries PublicationsShow
(-)-EpicatechinSweet cherryFruit, Drupes PublicationsShow
(-)-EpicatechinTeaTeas and herbal teas PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
(-)-Epicatechin 3'-O-Methyl-(-)-epicatechin 5-O-sulfatehuman ratplasma, plasma (major), urine, urine (major)host metabolism1h-3h50-200 nmol/L1-5%C16H16O9S384.051503269 Detailed Intervention Studies Publications
Cocoa Flavan-3-ols 3'-O-Methyl-(-)-epicatechin 5-O-sulfatehumanplasmahost metabolism1h-3h50-200 nmol/LNot AvailableC16H16O9S384.051503269 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Cocoa Flavan-3-ols 3'-O-Methyl-(-)-epicatechin 5-O-sulfateAgeDiscordant Publications
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