Identification

PhytoHub ID
PHUB001170
Name
Ferulic acid-4'-O-glucuronide
Systematic Name
3’-methoxycinnamic acid-4’-glucuronide
Synonyms
  • 3-methoxycinnamic acid-4-glucuronide
  • Ferulic acid-4-glucuronide
  • Ferulic acid-4'-glucuronide
  • trans-Ferulic acid glucuronide
CAS Number
Not Available
Average Mass
370.31
Monoisotopic Mass
370.08999678
Chemical Formula
C16H18O10
IUPAC Name
(2R,3R,4S,5S,6R)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
TWSIWBHKRJLZCF-XZYOHINHSA-N
InChI Identifier
InChI=1S/C16H18O10/c1-24-9-6-7(3-5-10(17)18)2-4-8(9)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-6,11-14,16,19-21H,1H3,(H,17,18)(H,22,23)/b5-3+/t11-,12+,13-,14+,16-/m0/s1
SMILES
[H]\C(=C(\[H])C1=CC(OC)=C(O[C@H]2O[C@H]([C@H](O)[C@H](O)[C@@H]2O)C(O)=O)C=C1)C(O)=O
Structure

Calculated Properties

Solubility (ALOGPS)
3.81e+00 g/l
LogS (ALOGPS)
-1.99
LogP (ALOGPS)
-0.23
Hydrogen Acceptors
10
Hydrogen Donors
5
Rotatable Bond Count
6
Polar Surface Area
162.98
Refractivity
83.5158
Polarizability
34.748538751337804
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.6868279760638365
pKa (strongest acidic)
2.9466244035891003
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Ferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Hazelnut Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Yerba mate Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Red Raspberries AnthocyaninsPolyphenolsFlavonoidsAnthocyaninsShow Food Phytochemical
Rosemary tea (poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Tomato (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Cranberry (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Blueberry (Poly)phenolsPolyphenolsNot specifiedNot AvailableShow Food Phytochemical
Olive oil (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Red grape pomace (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Globe artichoke (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Orange (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Oat (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(159.0440559,1.991746615);(161.0597059,1.449210095);(175.0389705,2.327024322);(177.0393644,2.041026869);(177.0546206,16.65911319);(195.0651853,11.67701079);(307.0812292,1.380533325);(309.0604938,1.632802227);(311.0761439,2.106794751);(325.0917939,1.86324689);(335.0761439,7.747367802);(353.0867085,22.53230399);(371.0972732,6.745779667)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(71.01275576,1.354159381);(123.0440559,1.33474861);(131.0491413,1.141509409);(135.0440559,2.238984433);(137.0597059,3.694689752);(147.0440559,5.447133383);(149.0597059,4.97530819);(151.075356,2.524622673);(159.0287997,1.680054862);(159.0440559,0.9145160377);(177.0393644,3.0829366);(177.0546206,20.83350171);(179.0338851,1.657229944);(179.0702706,1.792728874);(195.0651853,17.63975045);(307.0812292,1.385022043);(311.0761439,1.070694775);(325.0917939,1.694093919);(335.0761439,2.347444867);(353.0867085,3.642267267)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(25.00727645,0.6369546399);(43.01784114,0.7606023277);(59.01275576,1.105799339);(68.99710569,1.301361635);(71.01275576,1.664519301);(87.00767038,1.512969966);(92.99710569,0.8912315768);(105.0182351,0.6718229332);(115.002585,0.6339472124);(117.0182351,0.6552270562);(119.0127558,0.6977751569);(121.0284058,0.6577687325);(123.0440559,2.972935263);(131.0491413,4.26771639);(133.0647913,0.7717203792);(135.0440559,4.776939677);(137.0597059,7.60249905);(147.0440559,10.4186991);(149.0597059,5.291951793);(151.075356,1.390343176);(159.0287997,1.125912211);(161.0444498,1.346384725);(163.0389705,1.003996892);(163.0600999,0.8891956777);(175.0389705,1.066861631);(177.0393644,2.033296055);(177.0546206,5.58366297);(179.0338851,3.143357365);(195.0651853,6.550038495);(311.0761439,0.743573937);(335.0761439,0.7376822472)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(59.01385292,1.064327978);(71.01385292,1.373174002);(87.00876754,1.659226699);(89.0244176,1.78348151);(103.0036822,1.220132673);(117.0193322,1.970081769);(147.0298969,1.811539872);(149.0608031,0.9941695651);(175.0248115,1.89958033);(175.0400677,4.141885741);(177.0193322,1.123613872);(193.0353762,3.135418328);(193.0506323,12.56340924);(217.0506323,1.415120145);(235.061197,1.064598668);(247.061197,1.098204091);(307.0823264,3.570401987);(323.077241,2.84104306);(325.0928911,7.237517115);(351.0721556,8.926625853);(369.0827203,19.23741919)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(41.00328823,1.010477533);(43.0189383,0.8889929674);(59.01385292,2.533048617);(73.02950298,1.059756015);(87.00876754,1.462658793);(89.0244176,1.311483745);(103.0400677,1.483090433);(131.0349823,1.082539071);(145.0142468,0.7337631218);(147.0298969,1.521252274);(147.045153,2.566409898);(149.0608031,2.513850155);(161.0244176,0.9424248948);(163.0400677,0.7777259933);(175.0248115,2.235688026);(175.0400677,6.675822148);(177.0193322,6.51920611);(193.0353762,1.574187565);(193.0506323,18.04080611);(205.0506323,0.757858727);(235.061197,1.093296643);(279.0874118,0.8791510964);(281.1030618,0.8496864178);(307.0823264,4.488611359);(309.061591,2.275487321);(323.077241,1.956271216);(325.0928911,3.372515895);(339.0721556,0.7514347461);(351.0721556,5.353932038);(353.0514202,0.7167993426);(369.0827203,2.285119973)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00328823,1.290041363);(43.0189383,2.642251284);(59.01385292,6.000413675);(61.02950298,1.02149112);(71.01385292,0.8610680775);(73.02950298,1.501827476);(87.00876754,0.7958683951);(89.0244176,0.8007523883);(103.0400677,0.9282407373);(119.0349823,0.845973811);(121.029503,0.7278599428);(131.0349823,3.23173203);(133.029503,0.9563571854);(147.0298969,2.323619851);(147.045153,3.205222293);(149.0244176,2.070232268);(149.045547,1.047087492);(149.0608031,2.777190219);(151.0400677,0.7578686182);(161.0244176,2.315863975);(163.0400677,4.176191505);(165.0557177,0.7075784214);(175.0248115,0.7352762064);(175.0400677,6.519172794);(177.0193322,11.68364494);(191.0349823,1.755878769);(193.0506323,16.22787462);(281.0666763,1.628016176);(309.061591,0.6981678172)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Ferulic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
Ferulic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans PublicationsShow
Ferulic acidCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Ferulic acidCommon wheatCereals and cereal products PublicationsShow
Ferulic acidCornCereals and cereal products PublicationsShow
Ferulic acidDateFruit, Other fruits PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
Ferulic acidEggplantVegetables, Fruit vegetables PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
Ferulic acidFennelHerbs and Spices PublicationsShow
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidWhite wineBeverages, Alcoholic PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid Ferulic acid-4'-O-glucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Ferulic acid Ferulic acid-4'-O-glucuronideraturineNot AvailableNot AvailableNot AvailableNot AvailableC16H18O10370.08999678 Publications
Orange flavanones Ferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite1h-3h<20 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Hazelnut Flavan-3-ols Ferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available5-10%C16H18O10370.08999678 Detailed Intervention Studies Publications
Black tea Flavan-3-ols Ferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Ferulic acid-4'-O-glucuronidehumanplasma, urinehost metabolism1h-3h50-200 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids Ferulic acid-4'-O-glucuronidehumanplasma, urinehost metabolism1h-3h<20 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Red Raspberries Anthocyanins Ferulic acid-4'-O-glucuronidehumanplasma, urinehost metabolism1h-3h<20 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Rosemary tea (poly)phenols Ferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite8h-12h200-500 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Tomato (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasma, urinehost metabolism1h-3h200-500 nmol/L30-50%C16H18O10370.08999678 Detailed Intervention Studies Publications
Cranberry (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite8h-12h200-500 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Blueberry (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasmahost-gut microbiota co-metabolite3h-5h20-50 nmol/LNot AvailableC16H18O10370.08999678 Detailed Intervention Studies Publications
Olive oil (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasmahost-gut microbiota co-metaboliteNot Available0.5-2µmol/LNot AvailableC16H18O10370.08999678 Detailed Intervention Studies
Red grape pomace (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h50-200 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Globe artichoke (Poly)phenols Ferulic acid-4'-O-glucuronidehumanplasma, urinehost-gut microbiota co-metabolite5h-8h200-500 nmol/L<1%C16H18O10370.08999678 Detailed Intervention Studies Publications
Orange (Poly)phenols Ferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available1-5%C16H18O10370.08999678 Detailed Intervention Studies Publications
Oat (Poly)phenols Ferulic acid-4'-O-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available1-5%C16H18O10370.08999678 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

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