PhytoHub: Showing entry for Ferulic acid-4'-O-glucuronide

Ferulic acid-4'-O-glucuronide

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

86321-24-6

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

Similar Structures

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

External Links

No external links

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Caffeic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Ferulic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Orange flavanones	Polyphenols	Flavonoids	Flavanones	Show Food Phytochemical
Hazelnut Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Black tea Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Coffee Chlorogenic acids	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Yerba mate Chlorogenic acids	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Red Raspberries Anthocyanins	Polyphenols	Flavonoids	Anthocyanins	Show Food Phytochemical
Rosemary tea (poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Tomato (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Cranberry (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Blueberry (Poly)phenols	Polyphenols	Not specified	Not Available	Show Food Phytochemical
Olive oil (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Red grape pomace (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Globe artichoke (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Orange (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
Oat (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View 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/MS	Not Available	Positive	med	View 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/MS	Not Available	Positive	high	View 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/MS	Not Available	Negative	low	View 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/MS	Not Available	Negative	med	View 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/MS	Not Available	Negative	high	View 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 Phytochemical	Food Source	Food Source Group
Caffeic acid	American cranberry	Fruit, Berries	Publications	Show
Ferulic acid	American cranberry	Fruit, Berries	Publications	Show
Caffeic acid	Apple	Fruit, Pomes	Publications	Show
Caffeic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
Ferulic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
Caffeic acid	Beer	Beverages, Alcoholic	Publications	Show
Ferulic acid	Beer	Beverages, Alcoholic	Publications	Show
Ferulic acid	Bilberry	Fruit, Berries	Publications	Show
Ferulic acid	Black mulberry	Fruit, Berries	Publications	Show
Caffeic acid	Blackberry	Fruit, Berries	Publications	Show
Ferulic acid	Blackberry	Fruit, Berries	Publications	Show
Caffeic acid	Blueberry	Fruit, Berries	Publications	Show
Ferulic acid	Blueberry	Fruit, Berries	Publications	Show
Caffeic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Ferulic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Caffeic acid	Carrot	Vegetables, Root vegetables	Publications	Show
Caffeic acid	Cider	Beverages, Alcoholic	Publications	Show
Ferulic acid	Cocoa bean	Cocoa and cocoa products	Publications	Show
Caffeic acid	Coffee	Coffee and coffee products	Publications	Show
Ferulic acid	Coffee	Coffee and coffee products	Publications	Show
Ferulic acid	Common bean	Pulses and beans	Publications	Show
Ferulic acid	Common walnut	Nuts	Publications	Show
Caffeic acid	Common wheat	Cereals and cereal products	Publications	Show
Ferulic acid	Common wheat	Cereals and cereal products	Publications	Show
Ferulic acid	Corn	Cereals and cereal products	Publications	Show
Ferulic acid	Date	Fruit, Other fruits	Publications	Show
Caffeic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	European cranberry	Fruit, Berries	Publications	Show
Ferulic acid	European cranberry	Fruit, Berries	Publications	Show
Caffeic acid	European plum	Fruit, Drupes	Publications	Show
Ferulic acid	Fennel	Herbs and Spices	Publications	Show
Ferulic acid	Grapefruit	Fruit, Citrus	Publications	Show
Ferulic acid	Hard wheat	Cereals and cereal products	Publications	Show
Caffeic acid	Mate	Teas and herbal teas	Publications	Show
Caffeic acid	Olive, black	Fruit, Drupes	Publications	Show
Ferulic acid	Olive, black	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, green	Fruit, Drupes	Publications	Show
Ferulic acid	Olive, green	Fruit, Drupes	Publications	Show
Ferulic acid	Orange juice	Beverages, Non-alcoholic	Publications	Show
Caffeic acid	Pear	Fruit, Pomes	Publications	Show
Ferulic acid	Rapeseed	Oilseed crops	Publications	Show
Ferulic acid	Red raspberry	Fruit, Berries	Publications	Show
Ferulic acid	Rice	Cereals and cereal products	Publications	Show
Ferulic acid	Rosemary	Herbs and Spices	Publications	Show
Ferulic acid	Rye bread	Cereals and cereal products	Publications	Show
Ferulic acid	Spinach	Vegetables, Leaf vegetables	Publications	Show
Caffeic acid	Strawberry	Fruit, Berries	Publications	Show
Ferulic acid	Strawberry	Fruit, Berries	Publications	Show
Caffeic acid	Sweet cherry	Fruit, Drupes	Publications	Show
Ferulic acid	Sweet orange	Fruit, Citrus	Publications	Show
Ferulic acid	Tarragon	Herbs and Spices	Publications	Show
Caffeic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	White wine	Beverages, Alcoholic	Publications	Show
Caffeic acid	White wine grape	Fruit, Berries	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
Caffeic acid	Ferulic acid-4'-O-glucuronide	rat	plasma	Not Available	Not Available	Not Available	Not Available	C₁₆H₁₈O₁₀	370.08999678		Publications
Ferulic acid	Ferulic acid-4'-O-glucuronide	rat	urine	Not Available	Not Available	Not Available	Not Available	C₁₆H₁₈O₁₀	370.08999678		Publications
Orange flavanones	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	1h-3h	<20 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Hazelnut Flavan-3-ols	Ferulic acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	5-10%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Black tea Flavan-3-ols	Ferulic acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Coffee Chlorogenic acids	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	50-200 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Yerba mate Chlorogenic acids	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	<20 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Red Raspberries Anthocyanins	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	<20 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Rosemary tea (poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	8h-12h	200-500 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Tomato (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host metabolism	1h-3h	200-500 nmol/L	30-50%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Cranberry (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	8h-12h	200-500 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Blueberry (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma	host-gut microbiota co-metabolite	3h-5h	20-50 nmol/L	Not Available	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Olive oil (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma	host-gut microbiota co-metabolite	Not Available	0.5-2µmol/L	Not Available	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies
Red grape pomace (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	50-200 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Globe artichoke (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	200-500 nmol/L	<1%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Orange (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications
Oat (Poly)phenols	Ferulic acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%	C₁₆H₁₈O₁₀	370.08999678	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

Food Phytochemical	Metabolite	Effect	Value
Coffee Chlorogenic acids	Ferulic acid-4'-O-glucuronide	Microbiota	Effect, clusters	Publications
Tomato (Poly)phenols	Ferulic acid-4'-O-glucuronide	Microbiota	Effect, clusters	Publications
Red grape pomace (Poly)phenols	Ferulic acid-4'-O-glucuronide	Microbiota	Effect, clusters	Publications
Globe artichoke (Poly)phenols	Ferulic acid-4'-O-glucuronide	Microbiota	Effect, clusters	Publications

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