PhytoHub: Showing entry for Dihydrocaffeic acid-3'-O-glucuronide

Dihydrocaffeic acid-3'-O-glucuronide

Identification

PhytoHub ID

PHUB001204

Name

Dihydrocaffeic acid-3'-O-glucuronide

Systematic Name

3-(4'-hydroxyphenyl)propanoic acid-3'-glucuronide

Synonyms

3-(4-hydroxyphenyl)propanoic acid-3-glucuronide
3-(4-hydroxyphenyl)propionic acid-3-glucuronide
3-(4'-Hydroxyphenyl)propionic acid-3'-O-glucuronide
dihydrocaffeic acid-3-glucuronide

CAS Number

1187945-71-6

Average Mass

358.299

Monoisotopic Mass

358.08999678

Chemical Formula

C₁₅H₁₈O₁₀

IUPAC Name

(2R,3R,4R,5S,6R)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Key

AELQNMHOLDHBFA-VVSAWPALSA-N

InChI Identifier

InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m1/s1

SMILES

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

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 8.41e+00 g/l
LogS (ALOGPS): -1.63
LogP (ALOGPS): -0.09
Hydrogen Acceptors: 10
Hydrogen Donors: 6
Rotatable Bond Count: 6
Polar Surface Area: 173.98
Refractivity: 77.9402
Polarizability: 32.98813207252531
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -3.6868279761517333
pKa (strongest acidic): 3.0131597965048678
Number of Rings: 2
Rule of Five: No
Bioavailability: Yes
Ghose Filter: No
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: Phenylpropanoic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Dihydrocaffeic acid	Polyphenols	Phenolic acids	Phenolic acids subclass not specified	Show Food Phytochemical
Caffeic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Orange flavanones	Polyphenols	Flavonoids	Flavanones	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
Coffee hydroxycinnamates	Polyphenols	Phenolic acids	Hydroxycinnamic acids	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: ["1-hydroxy-2-unsubstituted benzenoids", "Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenol ethers", "Phenoxy compounds", "Phenylpropanoic acids", "Polyols", "Pyrans", "Secondary alcohols"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "1-o-glucuronide", "3-phenylpropanoic-acid", "Acetal", "Alcohol", "Aromatic heteromonocyclic compound", "Benzenoid", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "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", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Pyran", "Secondary alcohol"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(73.0289544,0.541641913);(87.00821896,0.4752440012);(99.00821896,0.4987269552);(109.0289544,0.377104538);(117.0187836,0.634828027);(119.0496898,0.7229862292);(123.0446045,1.202698306);(135.0446045,1.67091179);(137.0602545,1.499958722);(139.0759046,0.4314766565);(145.0289544,0.485816658);(147.0446045,3.207565396);(149.0602545,0.8166961291);(159.0293483,0.7215300852);(163.0395191,1.927743078);(165.0551691,13.90931579);(167.0708192,2.512353146);(177.039913,2.510571433);(183.0657338,17.92954285);(195.0504777,0.4604885217);(281.0661278,0.7428207388);(285.0610424,0.3796269157);(295.0817778,1.445972886);(297.0610424,0.5508356908);(297.0974279,0.3842258225);(299.0766924,1.958390174);(313.0923425,2.554114974);(315.1079926,0.4113335587);(323.0766924,8.754662321);(341.0872571,17.66530583);(359.0978218,12.61551087)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(71.01330434,0.7081148541);(73.0289544,1.609932224);(109.0289544,1.329429275);(119.0496898,1.33315774);(121.0653399,0.6039127087);(123.0446045,4.267451687);(125.0602545,1.003819719);(135.0446045,8.336890339);(137.0602545,6.466743241);(139.0759046,2.876025353);(147.0446045,1.733958434);(151.0395191,0.8410654055);(153.0551691,2.819310377);(159.0293483,2.380992545);(163.0395191,1.070657543);(165.0551691,17.01982069);(167.0708192,2.684696424);(177.039913,3.472062945);(181.0500838,0.6679840624);(183.0657338,23.64579937);(281.0661278,0.5877174134);(295.0817778,1.671880792);(297.0974279,0.5714389022);(299.0766924,0.7687999061);(311.0766924,0.5147699339);(313.0923425,2.060335332);(315.1079926,0.6272606689);(323.0766924,2.843453253);(329.0872571,0.7520625701);(341.0872571,3.476562477);(359.0978218,1.253893816)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(43.01838972,2.031829275);(61.0289544,0.8867406897);(71.01330434,1.830224603);(73.0289544,2.173054339);(87.00821896,2.89292291);(89.02386902,0.8864071658);(95.01330434,1.442085648);(105.0187836,1.027691453);(107.0496898,1.04136273);(109.0289544,3.980092521);(117.0187836,1.870282119);(119.0496898,6.158189992);(121.0289544,1.419502401);(121.0653399,1.447240431);(123.0446045,11.82762696);(125.0602545,1.8214424);(131.0344337,0.8809583204);(135.0446045,17.02232111);(137.0602545,7.589082066);(139.0759046,2.330897493);(159.0293483,1.873724913);(161.0449984,1.896140329);(163.0395191,1.378663069);(163.0606485,1.430578839);(165.0551691,8.943131694);(169.0864693,1.219885057);(177.039913,2.158812031);(183.0657338,7.484611902);(297.0610424,1.090455434);(299.0766924,0.9941396333);(323.0766924,0.9699024726)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(41.00273965,0.7213455207);(56.99765427,1.187406006);(59.01330434,1.95126022);(71.01330434,1.792632409);(73.0289544,0.634690345);(87.00821896,2.187758833);(89.02386902,2.542701687);(103.0031336,1.519358175);(117.0187836,2.590398065);(135.0446045,0.9837936204);(137.0602545,1.713531556);(147.0293483,2.390021854);(149.0449984,0.884271606);(163.0242629,0.8299820383);(163.0395191,2.168239563);(175.0242629,1.833957119);(177.0551691,0.7641294413);(181.0500838,18.23866283);(193.0348276,3.915648065);(205.0500838,0.6673968344);(207.0657338,0.7814904963);(223.0606485,1.247924356);(239.0555631,0.7955135765);(253.0712131,0.5887764343);(269.1025133,0.9101836967);(295.0817778,2.882059609);(311.0766924,3.504393719);(313.0923425,9.735225118);(327.0716071,0.6171444769);(339.0716071,4.248796806);(357.0821717,25.17130592)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,1.310179557);(59.01330434,5.65754063);(73.0289544,1.62711212);(87.00821896,2.152325268);(89.02386902,2.048883888);(103.0395191,2.165886045);(117.0187836,0.9518948329);(121.0289544,2.470099974);(131.0344337,1.117365785);(133.0289544,1.269742273);(135.0446045,4.847025636);(137.0602545,5.430705871);(145.0136983,1.006739066);(147.0293483,2.179081147);(149.0449984,0.9210246581);(153.0551691,1.185696673);(163.0395191,6.807375812);(175.0242629,2.493098212);(181.0500838,28.2979301);(193.0348276,1.959474429);(193.0500838,0.9609424476);(223.0606485,1.220710539);(239.0555631,0.9381608489);(267.0868632,1.331150311);(269.1025133,1.349348616);(295.0817778,3.846793216);(311.0766924,2.485819204);(313.0923425,5.170102456);(339.0716071,2.432166162);(339.0716071,0.9637334099);(357.0821717,3.40189081)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,1.584651822);(43.01838972,3.565955512);(44.99765427,1.417116219);(56.99765427,0.8877409697);(59.01330434,18.00924305);(61.0289544,3.981085181);(71.01330434,1.357184677);(73.0289544,2.587802937);(84.99256889,0.5301055389);(87.00821896,1.294880516);(89.02386902,0.8824508682);(91.03951908,0.7382287154);(103.0395191,1.128872775);(107.0133043,0.5875861477);(107.0496898,0.5693276937);(117.0187836,0.6448144386);(121.0289544,2.296563685);(123.0446045,0.7698109296);(131.0344337,3.943459213);(133.0289544,1.473191037);(135.0446045,6.012871143);(137.0602545,6.67098335);(147.0293483,2.939912306);(149.023869,0.5835533196);(149.0449984,1.32137093);(151.0395191,1.717085714);(161.023869,0.7657054381);(163.0395191,7.889047261);(179.0344337,1.773523341);(181.0500838,21.37659488);(251.0555631,0.6992803936)

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
Caffeic acid	Apple	Fruit, Pomes	Publications	Show
Caffeic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
Caffeic acid	Beer	Beverages, Alcoholic	Publications	Show
Caffeic acid	Blackberry	Fruit, Berries	Publications	Show
Dihydrocaffeic acid	Blueberry	Fruit, Berries		Show
Caffeic acid	Blueberry	Fruit, Berries	Publications	Show
Dihydrocaffeic acid	Broccoli	Vegetables, Cabbages		Show
Caffeic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Caffeic acid	Carrot	Vegetables, Root vegetables	Publications	Show
Dihydrocaffeic acid	Cider	Beverages, Alcoholic		Show
Caffeic acid	Cider	Beverages, Alcoholic	Publications	Show
Dihydrocaffeic acid	Coffee	Coffee and coffee products		Show
Caffeic acid	Coffee	Coffee and coffee products	Publications	Show
Dihydrocaffeic acid	Common wheat	Cereals and cereal products		Show
Caffeic acid	Common wheat	Cereals and cereal products	Publications	Show
Dihydrocaffeic acid	Corn	Cereals and cereal products		Show
Caffeic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	European cranberry	Fruit, Berries	Publications	Show
Caffeic acid	European plum	Fruit, Drupes	Publications	Show
Dihydrocaffeic acid	Grapes	Fruit, Berries		Show
Dihydrocaffeic acid	Lemon	Fruit, Citrus		Show
Dihydrocaffeic acid	Lettuce	Vegetables, Leaf vegetables		Show
Dihydrocaffeic acid	Lime	Fruit, Citrus		Show
Caffeic acid	Mate	Teas and herbal teas	Publications	Show
Dihydrocaffeic acid	Olive, black	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, black	Fruit, Drupes	Publications	Show
Dihydrocaffeic acid	Olive, green	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, green	Fruit, Drupes	Publications	Show
Caffeic acid	Pear	Fruit, Pomes	Publications	Show
Dihydrocaffeic acid	Spinach	Vegetables, Leaf vegetables		Show
Caffeic acid	Strawberry	Fruit, Berries	Publications	Show
Caffeic acid	Sweet cherry	Fruit, Drupes	Publications	Show
Caffeic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Dihydrocaffeic acid	Wheat bread	Cereals and cereal products		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
Dihydrocaffeic acid	Dihydrocaffeic acid-3'-O-glucuronide	rat	urine	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₈O₁₀	358.08999678		Publications
Caffeic acid	Dihydrocaffeic acid-3'-O-glucuronide	human	plasma	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₈O₁₀	358.08999678		Publications
Orange flavanones	Dihydrocaffeic acid-3'-O-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₈O₁₀	358.08999678	Detailed Intervention Studies
Black tea Flavan-3-ols	Dihydrocaffeic acid-3'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₅H₁₈O₁₀	358.08999678	Detailed Intervention Studies	Publications
Coffee Chlorogenic acids	Dihydrocaffeic acid-3'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₅H₁₈O₁₀	358.08999678	Detailed Intervention Studies	Publications
Yerba mate Chlorogenic acids	Dihydrocaffeic acid-3'-O-glucuronide	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₁₅H₁₈O₁₀	358.08999678	Detailed Intervention Studies	Publications
Coffee hydroxycinnamates	Dihydrocaffeic acid-3'-O-glucuronide	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₈O₁₀	358.08999678	Detailed Intervention Studies

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	Coffee Chlorogenic acids		Dihydrocaffeic acid-3'-O-glucuronide	Microbiota	Effect, clusters	Publications

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