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

Coumaric acid-4'-O-glucuronide

Identification

PhytoHub ID

PHUB001198

Name

Coumaric acid-4'-O-glucuronide

Systematic Name

Cinnamic acid-4'-glucuronide

Synonyms

cinnamic acid-4-glucuronide
cinnamic acid-4-O-glucuronide
trans-Coumaric acid glucuronide

CAS Number

Not Available

Average Mass

340.284

Monoisotopic Mass

340.079432095

Chemical Formula

C₁₅H₁₆O₉

IUPAC Name

(2S,3S,4R,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Key

SOKJXEKPKWKYKR-LZJCFMAWSA-N

InChI Identifier

InChI=1S/C15H16O9/c16-9(17)6-3-7-1-4-8(5-2-7)23-15-12(20)10(18)11(19)13(24-15)14(21)22/h1-6,10-13,15,18-20H,(H,16,17)(H,21,22)/b6-3+/t10-,11+,12-,13+,15-/m1/s1

SMILES

O[C@H]1[C@H](OC2=CC=C(\C=C\C(O)=O)C=C2)O[C@@H]([C@@H](O)[C@H]1O)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 4.66e+00 g/l
LogS (ALOGPS): -1.86
LogP (ALOGPS): -0.20
Hydrogen Acceptors: 9
Hydrogen Donors: 5
Rotatable Bond Count: 5
Polar Surface Area: 153.75
Refractivity: 77.0526
Polarizability: 31.542269323330146
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -3.6868267613833194
pKa (strongest acidic): 3.068216278643664
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
Coumaric acid (p-)	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Orange flavanones	Polyphenols	Flavonoids	Flavanones	Show Food Phytochemical
Coffee Chlorogenic acids	Polyphenols	Phenolic acids	Hydroxycinnamic acids	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

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Organooxygen compounds
Super-class: Organic oxygen compounds
Sub-class: Carbohydrates and carbohydrate conjugates
Direct Parent Name: Phenolic glycosides
Alternative Parent Names: ["Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenol ethers", "Phenoxy compounds", "Polyols", "Pyrans", "Secondary alcohols", "Styrenes"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-o-glucuronide", "Acetal", "Alcohol", "Aromatic heteromonocyclic compound", "Benzenoid", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Cinnamic acid or derivatives", "Dicarboxylic acid or derivatives", "Glucuronic acid or derivatives", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Monocyclic benzene moiety", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organoheterocyclic compound", "Oxacycle", "Oxane", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Pyran", "Secondary alcohol", "Styrene"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(145.0284058,1.840118143);(147.0440559,17.47342281);(165.0546206,12.24149703);(177.0393644,1.68011842);(277.0706646,1.46501454);(279.0499291,1.703754758);(281.0655792,2.215287556);(295.0812292,1.974202566);(305.0655792,8.391647762);(323.0761439,24.06269336);(341.0867085,7.077000536)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(101.0385766,1.949929295);(105.0334912,2.397918235);(107.0491413,3.720604466);(117.0334912,5.813693709);(119.0491413,4.906808477);(121.0647913,2.156680957);(129.0334912,1.82214249);(147.0440559,25.0105306);(149.0597059,1.754296979);(159.0287997,1.654094397);(165.0546206,17.70785983);(177.0393644,2.64138004);(277.0706646,1.300694459);(295.0812292,1.590314715);(305.0655792,2.268768296);(323.0761439,3.537003524)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(25.00727645,0.6813712692);(43.01784114,0.8151272215);(59.01275576,1.346837005);(68.99710569,1.517706149);(71.01275576,1.681716536);(84.99202031,0.6208573183);(87.00767038,1.600714122);(89.03857658,0.904280662);(95.04914126,1.649864193);(101.0385766,3.113881528);(103.002585,0.6212454954);(103.0542266,0.7579838606);(105.0182351,0.7095726311);(105.0334912,6.163868423);(107.0491413,8.94408131);(115.002585,0.6622472266);(117.0182351,0.8531006101);(117.0334912,12.86864601);(119.0491413,6.002414874);(121.0647913,1.739924278);(137.0597059,1.01126502);(145.0284058,0.9138985961);(147.0440559,8.636869095);(157.0131497,0.6835135462);(159.0287997,1.178657728);(161.0444498,1.443627392);(165.0546206,7.629688378);(177.0393644,0.6713172545);(277.0706646,0.6386188627);(281.0655792,0.8129436521);(305.0655792,0.7992504592)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(59.01385292,1.023932532);(71.01385292,1.454461092);(87.00876754,1.148840654);(89.0244176,1.924306719);(103.0036822,1.152408636);(117.0193322,1.858244374);(119.0502384,1.150848667);(145.029503,6.365181859);(147.0298969,1.429756696);(163.0400677,13.92248799);(175.0248115,1.191448212);(187.0400677,1.472778697);(205.0506323,1.10870471);(217.0506323,1.131279971);(277.0717617,3.855601265);(293.0666763,2.983045617);(295.0823264,7.752942498);(321.061591,9.375335062);(339.0721556,20.42058239)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(41.00328823,1.051097037);(43.0189383,1.000543958);(59.01385292,2.349002325);(73.02950298,1.185094815);(87.00876754,1.508828915);(89.0244176,1.456063689);(103.0400677,1.707813176);(117.0345884,3.728019063);(119.0502384,4.063864646);(131.0349823,1.290584561);(145.029503,9.84051796);(147.0298969,1.251218276);(163.0400677,23.02811337);(175.0248115,1.752661673);(175.0400677,0.8025431142);(193.0353762,1.358095403);(205.0506323,1.117311648);(249.0768471,1.052229913);(251.0924972,1.068861943);(277.0717617,5.337304863);(293.0666763,2.095471011);(295.0823264,3.928652528);(321.061591,5.808229893);(339.0721556,2.526039439)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00328823,1.544906721);(43.0189383,3.276680408);(44.99820285,1.571306469);(59.01385292,3.997232589);(61.02950298,0.962755831);(71.01385292,0.9784691816);(73.02950298,1.918693973);(103.0400677,1.137500745);(117.0345884,6.700924586);(119.0502384,7.557695381);(131.0349823,3.431490849);(133.029503,0.9113477458);(135.045153,1.285350141);(145.029503,17.86924213);(147.0298969,0.973795208);(161.0244176,1.993704393);(163.0400677,24.07177243)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Coumaric acid (p-)	American cranberry	Fruit, Berries	Publications	Show
Coumaric acid (p-)	Apple	Fruit, Pomes	Publications	Show
Coumaric acid (p-)	Apple cider	Beverages, Alcoholic	Publications	Show
Coumaric acid (p-)	Apple juice	Beverages, Non-alcoholic	Publications	Show
Coumaric acid (p-)	Beer	Beverages, Alcoholic	Publications	Show
Coumaric acid (p-)	Blackberry	Fruit, Berries	Publications	Show
Coumaric acid (p-)	Coffee	Coffee and coffee products	Publications	Show
Coumaric acid (p-)	European cranberry	Fruit, Berries	Publications	Show
Coumaric acid (p-)	Olive, black	Fruit, Drupes	Publications	Show
Coumaric acid (p-)	Olive, green	Fruit, Drupes	Publications	Show
Coumaric acid (p-)	Orange juice	Beverages, Non-alcoholic	Publications	Show
Coumaric acid (p-)	Peanut	Nuts	Publications	Show
Coumaric acid (p-)	Strawberry	Fruit, Berries	Publications	Show
Coumaric acid (p-)	Tomato	Vegetables, Fruit vegetables	Publications	Show
Coumaric acid (p-)	Wheat bread	Cereals and cereal products	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
Coumaric acid (p-)	Coumaric acid-4'-O-glucuronide	rat	plasma	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₆O₉	340.079432095		Publications
Orange flavanones	Coumaric acid-4'-O-glucuronide	human	urine	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₆O₉	340.079432095	Detailed Intervention Studies	Publications
Coffee Chlorogenic acids	Coumaric acid-4'-O-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	1h-3h	<20 nmol/L	<1%	C₁₅H₁₆O₉	340.079432095	Detailed Intervention Studies	Publications
Tomato (Poly)phenols	Coumaric acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	5-10%	C₁₅H₁₆O₉	340.079432095	Detailed Intervention Studies	Publications
Cranberry (Poly)phenols	Coumaric acid-4'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₅H₁₆O₉	340.079432095	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Coumaric acid-4'-O-glucuronide