metabolite

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

Identification

PhytoHub ID
PHUB001205
Name
Dihydrocaffeic acid-4'-O-glucuronide
Systematic Name
3-(3'-hydroxyphenyl)propanoic acid-4'-glucuronide
Synonyms
  • 3-(3-hydroxyphenyl)propanoic acid-4-glucuronide
  • 3-(3-hydroxyphenyl)propionic acid-4-glucuronide
  • dihydrocaffeic acid-4-glucuronide
CAS Number
Not Available
Average Mass
358.299
Monoisotopic Mass
358.08999678
Chemical Formula
C15H18O10
IUPAC Name
(2S,3S,4S,5R)-6-[4-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
DUTJMLCURMYWCW-HXMBFPRCSA-N
InChI Identifier
InChI=1S/C15H18O10/c16-7-5-6(2-4-9(17)18)1-3-8(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?/m0/s1
SMILES
O[C@@H]1[C@@H](O)C(OC2=C(O)C=C(CCC(O)=O)C=C2)O[C@@H]([C@H]1O)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
7.58e+00 g/l
LogS (ALOGPS)
-1.67
LogP (ALOGPS)
-0.05
Hydrogen Acceptors
10
Hydrogen Donors
6
Rotatable Bond Count
6
Polar Surface Area
173.98
Refractivity
77.94019999999999
Polarizability
33.025159771236915
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.686827975275015
pKa (strongest acidic)
2.9585986983937547
Number of Rings
2
Rule of Five
No
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Dihydrocaffeic acidPolyphenolsPhenolic acidsPhenolic acids subclass not specifiedShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow 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", "1-hydroxy-4-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-hydroxy-4-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 TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(73.0289544,0.5719050162);(87.00821896,0.4741270848);(99.00821896,0.496240476);(109.0289544,0.3887076245);(117.0187836,0.6335951611);(119.0496898,0.7357461806);(123.0446045,1.258162658);(135.0446045,1.662498916);(137.0602545,1.49248045);(139.0759046,0.4293254639);(147.0446045,3.181342719);(149.0602545,0.830806881);(159.0293483,0.7179327871);(163.0395191,2.072916556);(165.0551691,13.81319906);(167.0708192,2.55673342);(177.039913,2.506482543);(183.0657338,17.84014807);(195.0504777,0.4597032936);(281.0661278,0.7675479271);(285.0610424,0.3789062288);(295.0817778,1.44255559);(297.0610424,0.5480892854);(297.0974279,0.3836634457);(299.0766924,2.020119037);(311.0766924,0.3572228519);(313.0923425,2.541380217);(315.1079926,0.4092826921);(323.0766924,8.801707589);(341.0872571,17.67486436);(359.0978218,12.55260641)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(71.01330434,0.7053473968);(73.0289544,1.743319699);(109.0289544,1.259417825);(119.0496898,1.353714579);(121.0653399,0.594362129);(123.0446045,4.316879842);(125.0602545,1.03028919);(135.0446045,8.315774149);(137.0602545,6.452186988);(139.0759046,2.869551592);(147.0446045,1.689901292);(151.0395191,0.8391722176);(153.0551691,2.812964278);(159.0293483,2.375633073);(163.0395191,1.154216125);(165.0551691,16.93528498);(167.0708192,2.705466479);(177.039913,3.470834345);(181.0500838,0.6662000256);(183.0657338,23.58272503);(281.0661278,0.5949563114);(295.0817778,1.669309451);(297.0974279,0.5713335339);(299.0766924,0.779488375);(311.0766924,0.5141805805);(313.0923425,2.053739342);(315.1079926,0.6256317873);(323.0766924,2.848003983);(329.0872571,0.7501652291);(341.0872571,3.471321095);(359.0978218,1.248629075)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(43.01838972,1.307097962);(61.0289544,0.8905998631);(71.01330434,1.82371239);(73.0289544,2.578447838);(87.00821896,2.905802921);(89.02386902,0.8902731298);(95.01330434,1.163141089);(105.0187836,1.032165663);(109.0289544,3.852905102);(117.0187836,1.878642663);(119.0496898,6.415959553);(121.0289544,1.425679361);(121.0653399,1.461398773);(123.0446045,12.11696609);(125.0602545,1.867695345);(131.0344337,0.8847847476);(135.0446045,17.07908971);(137.0602545,7.622045112);(139.0759046,2.341021706);(159.0293483,1.881863404);(161.0449984,1.904376181);(163.0395191,1.366210588);(163.0606485,1.436792533);(165.0551691,8.961838533);(169.0864693,1.22540802);(177.039913,2.198553735);(183.0657338,7.518171652);(221.0449984,0.897985004);(297.0610424,1.095276557);(299.0766924,1.001335646);(323.0766924,0.9747591316)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(41.00273965,0.7219420004);(56.99765427,1.188386726);(59.01330434,1.951474515);(71.01330434,1.794114735);(73.0289544,0.6352151696);(87.00821896,2.188991332);(89.02386902,2.543673083);(103.0031336,1.51970466);(117.0187836,2.591086419);(135.0446045,0.9847238796);(137.0602545,1.714948473);(147.0293483,2.390720149);(149.0449984,0.8848063214);(163.0242629,0.8300871655);(163.0395191,2.169603187);(175.0242629,1.834601514);(177.0551691,0.7647613232);(181.0500838,18.2429635);(193.0348276,3.914692202);(205.0500838,0.6679794332);(207.0657338,0.7821380437);(223.0606485,1.248182765);(239.0555631,0.7956619125);(253.0712131,0.5889154979);(269.1025133,0.9109363264);(295.0817778,2.884450699);(311.0766924,3.504487361);(313.0923425,9.733410408);(327.0716071,0.6173315504);(339.0716071,4.248806541);(357.0821717,25.15120311)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(43.01838972,1.311960502);(59.01330434,5.659037273);(73.0289544,1.629323875);(87.00821896,2.154410908);(89.02386902,2.051133822);(103.0395191,2.168830162);(117.0187836,0.9529542931);(121.0289544,2.477089468);(131.0344337,1.118884635);(133.0289544,1.270771043);(135.0446045,4.831603107);(137.0602545,5.438087901);(145.0136983,1.007777673);(147.0293483,2.181167023);(149.0449984,0.9222248864);(153.0551691,1.119491398);(163.0395191,6.815921036);(175.0242629,2.495576778);(181.0500838,28.32252091);(193.0348276,1.960095153);(193.0500838,0.9618187356);(223.0606485,1.222200399);(239.0555631,0.9388158865);(267.0868632,1.332959761);(269.1025133,1.351182804);(295.0817778,3.852322226);(311.0766924,2.486840121);(313.0923425,5.170034378);(339.0716071,2.433327499);(339.0716071,0.9638102211);(357.0821717,3.397826124)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,1.581983617);(43.01838972,3.559951226);(44.99765427,1.414729047);(56.99765427,0.8862460945);(59.01330434,18.21338996);(61.0289544,3.974766445);(71.01330434,1.354899476);(73.0289544,2.583445645);(84.99256889,0.5292101899);(87.00821896,1.292689462);(89.02386902,0.8809632771);(91.03951908,0.7369752336);(103.0395191,1.126972001);(107.0133043,0.5865967816);(117.0187836,0.643717652);(121.0289544,2.255038286);(123.0446045,0.85287568);(131.0344337,3.936819293);(133.0289544,1.334200952);(135.0446045,6.018210579);(137.0602545,6.65975088);(147.0293483,2.934955739);(149.023869,0.5825696213);(149.0449984,1.319145044);(151.0395191,1.577385883);(161.023869,0.7645296237);(163.0395191,7.877755017);(177.0187836,0.5194674284);(179.0344337,1.962296223);(181.0500838,21.34036463);(251.0555631,0.698099014)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Dihydrocaffeic acidCommon wheatCereals and cereal productsShow
Dihydrocaffeic acidCornCereals and cereal productsShow
Dihydrocaffeic acidGrapesFruit, BerriesShow
Dihydrocaffeic acidLemonFruit, CitrusShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Dihydrocaffeic acidOlive, blackFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, greenFruit, Drupes PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Dihydrocaffeic acidWheat breadCereals and cereal productsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Dihydrocaffeic acid Dihydrocaffeic acid-4'-O-glucuronideraturineNot AvailableNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Publications
Orange flavanones Dihydrocaffeic acid-4'-O-glucuronideNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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