metabolite

Showing entry for 3-(3,5-Dihydroxyphenyl)propanoic acid

Identification

PhytoHub ID
PHUB001381
Name
3-(3,5-Dihydroxyphenyl)propanoic acid
Systematic Name
3-(3',5'-dihydroxyphenyl)propanoic acid
Synonyms
  • 3-(3,5-dihydroxyphenyl)propionic acid
  • 3-(3',5'-dihydroxyphenyl)propionic acid
  • 3,5-dihydroxy-dihydrocinnamic acid
  • 3,5-dihydroxy-hydrocinnamic acid
  • 3,5-dihydroxybenzenepropanoic acid
  • DHPPA
CAS Number
26539-01-5
Average Mass
182.175
Monoisotopic Mass
182.057908802
Chemical Formula
C9H10O4
IUPAC Name
3-(3,5-dihydroxyphenyl)propanoic acid
InChI Key
ITPFIKQWNDGDLG-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)
SMILES
OC(=O)CCC1=CC(O)=CC(O)=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
Not Available
LogS (ALOGPS)
Not Available
LogP (ALOGPS)
Not Available
Hydrogen Acceptors
4
Hydrogen Donors
3
Rotatable Bond Count
3
Polar Surface Area
77.76
Refractivity
45.9284
Polarizability
17.891032264898218
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.670873250005126
pKa (strongest acidic)
3.817707159108314
Number of Rings
1
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
Alkylresorcinol metabolites
Sub-class
Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
5-NonadecylresorcinolPolyphenolsAlkylresorcinolsNot AvailableShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Phenylpropanoic acids
Super-class
Phenylpropanoids and polyketides
Sub-class
Not Available
Direct Parent Name
Phenylpropanoic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Resorcinols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Resorcinol"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(29.00219012,0.7847995388);(41.00219012,1.348502255);(43.98927962,1.38498422);(44.99710422,5.547029577);(46.00492882,1.00105649);(55.05422362,0.7851528184);(59.01275342,2.410766924);(65.03857442,1.574345806);(67.05422362,0.8855204085);(81.03348852,0.8944681501);(83.01275342,0.7248567234);(107.0491377,0.7251065535);(110.0362272,3.562822737);(111.0440518,2.200305014);(112.0518764,1.342191886);(113.059701,1.199772315);(122.0362272,4.218513026);(123.0440518,17.02021786);(124.0474536,1.364296091);(134.0362272,1.420083404);(135.0440518,3.415327348);(136.0518764,9.578815529);(137.0552772,0.876474268);(137.059701,6.79966483);(138.0675256,5.262318125);(163.0389659,1.003392123);(164.0467905,3.531760857);(165.0546151,4.414609452);(181.0495292,5.4472552);(182.0573538,8.403743364);(183.0607639,0.8718471034)
Predicted GC-MSGC-MSPositiveNot AvailableView Spectrum(59.03115062,1.183187728);(71.03115062,1.127197815);(72.03897522,0.9721474749);(73.04679982,13.14520014);(74.04796012,1.124785302);(74.05462442,0.9158611389);(75.02606472,4.889526489);(75.06244902,0.8826262292);(88.03388932,0.8722567121);(89.04171392,4.40413976);(90.04953852,1.707208256);(91.05736312,1.461071033);(117.036628,1.587399692);(131.0522772,1.308746771);(265.1074502,1.441574113);(266.1152748,0.8528490913);(267.1230994,7.290047389);(268.1249694,1.829727601);(269.1222914,0.7248080114);(280.130924,1.080780819);(281.1387486,4.942530115);(282.140687,1.297333941);(309.1336627,3.835712648);(310.1356621,1.051186988);(311.1129276,0.8643557916);(325.1285768,2.514043102);(326.1364014,2.600904267);(327.144226,1.455352691);(383.1524514,5.457867528);(384.154198,1.90124677);(385.1519929,0.8992429404)
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(43.98927962,1.130445183);(44.99710422,4.527569895);(46.00492882,0.8170775308);(59.01275342,1.935401371);(110.0362272,2.908030098);(111.0440518,1.796295296);(112.0518764,1.095517428);(113.059701,0.9792724091);(122.0362272,3.749167573);(123.0440518,18.42340411);(124.0474536,1.476771826);(134.0362272,1.297354845);(135.0440518,4.142231941);(136.0518764,8.374443728);(137.059701,8.642560508);(138.0631065,0.792102276);(138.0675256,3.936947371);(164.0467905,2.952358625);(165.0546151,1.840827946);(180.0417046,1.57862491);(181.0495292,1.203656265);(182.0573538,6.878951231)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(27.0234751,0.1065640396);(43.01838972,0.0939697634);(44.99765427,0.1037793559);(49.0289544,0.0533751197);(55.01838972,0.4722259276);(71.01330434,0.3828837611);(73.0289544,0.996599525);(79.01838972,0.0478616778);(81.03403978,0.0328186902);(95.01330434,0.1164374241);(95.04968984,0.0435624337);(97.0289544,0.069425433);(99.04460446,0.0826997633);(111.0446045,0.7811848323);(113.0602545,0.0997532956);(115.0759046,0.0315103475);(119.0496898,0.1307362764);(121.0289544,0.0586089725);(123.0446045,0.0599287308);(135.0446045,1.088567739);(137.023869,0.0974564868);(137.0602545,10.10199773);(139.0395191,0.0780072876);(139.0759046,1.017628882);(141.0551691,0.0780947529);(147.0446045,0.6342823366);(149.023869,0.1071823051);(153.0551691,0.0518082822);(165.0551691,37.04785844);(167.0344337,0.4174752659);(183.0657338,45.51571512)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(27.0234751,0.7148980962);(51.0234751,0.292860545);(53.03912516,0.822347298);(55.01838972,1.651840297);(71.01330434,1.205203205);(73.0289544,2.740582909);(79.01838972,0.4062381005);(81.03403978,0.5120696033);(93.03403978,0.3011739729);(95.01330434,0.6296086832);(95.04968984,0.5922165249);(97.0289544,0.5627603511);(99.04460446,0.6953954842);(109.0653399,0.1747410879);(111.0446045,1.642688746);(113.0602545,0.2150094499);(119.0496898,1.294543271);(121.0289544,0.3010816405);(121.0653399,0.2778069815);(123.0446045,0.3707567673);(135.0446045,2.186744712);(137.023869,0.3066289872);(137.0602545,31.58375055);(139.0395191,0.4137251586);(139.0759046,2.687966882);(141.0551691,0.3001757795);(147.0446045,1.923189424);(153.0551691,0.7915030537);(165.0551691,27.5414431);(167.0344337,0.2194132674);(183.0657338,16.64163606)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,7.136217541);(29.03912516,1.02378385);(44.99765427,1.110935671);(51.0234751,5.948024984);(53.03912516,4.517037452);(55.01838972,2.901039019);(67.05477522,7.299570794);(69.07042529,0.6351687173);(71.01330434,2.060652399);(73.0289544,2.208480904);(79.01838972,1.32021024);(81.03403978,0.9777717132);(93.03403978,5.993881917);(95.01330434,3.113505909);(95.04968984,4.811198026);(109.0653399,1.642332643);(111.0446045,3.19607883);(113.0602545,0.8630966325);(117.0340398,2.839237513);(119.0133043,1.38437506);(119.0496898,8.575684035);(121.0289544,1.388828408);(121.0653399,2.243677313);(123.0446045,1.658989439);(135.0446045,4.937010297);(137.023869,0.7002732859);(137.0602545,13.51954589);(139.0759046,2.420918008);(147.0446045,0.8452157102);(165.0551691,2.186200273);(167.0344337,0.5410575221)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(17.00273965,0.0367294551);(29.00273965,0.0081515663);(41.00273965,0.3074025514);(43.01838972,0.1103354429);(44.99765427,0.1631895146);(47.01330434,0.0218839033);(57.03403978,0.0217891987);(65.03912516,0.025689014);(67.05477522,0.0320031058);(71.01330434,0.0218896286);(83.01330434,0.0469227276);(93.03403978,0.0482509208);(95.01330434,0.0075533718);(95.04968984,0.051099073);(97.0289544,0.0276472599);(109.0289544,0.3075744142);(111.0446045,0.3490925544);(113.0602545,0.0311785048);(119.0496898,0.3071269924);(121.0289544,0.0138651691);(133.0289544,0.1518003273);(135.008219,0.0550050489);(135.0446045,0.8332152127);(137.023869,0.1044375065);(137.0602545,13.14473557);(139.0395191,0.235576747);(145.0289544,0.0154983246);(151.0395191,0.1216319607);(163.0395191,4.499884847);(165.0187836,0.0704088006);(181.0500838,78.82843128)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(17.00273965,0.2207842817);(41.00273965,0.2588034512);(43.01838972,0.0493847725);(44.99765427,1.293705418);(47.01330434,0.0859379422);(65.03912516,0.1991168697);(67.05477522,0.1678813363);(71.01330434,0.0920896254);(83.01330434,0.0646280422);(91.01838972,0.0709841367);(93.03403978,0.4413284875);(95.01330434,0.0416310259);(95.04968984,1.011658522);(97.0289544,0.1755287998);(107.0496898,0.1369095784);(109.0289544,0.7872666953);(111.0446045,0.4822229864);(113.0602545,0.1651315411);(119.0496898,1.376077318);(121.0289544,0.2576369178);(133.0289544,1.214695704);(135.008219,0.425830101);(135.0446045,3.217834408);(137.023869,1.015524069);(137.0602545,24.69975713);(139.0395191,1.732922633);(145.0289544,0.0811576463);(151.0395191,0.3801461025);(163.0395191,8.23159538);(165.0187836,0.2553741866);(181.0500838,51.36645489)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(29.00273965,1.81566782);(41.00273965,4.258407847);(44.99765427,7.957350422);(53.00273965,0.8787022951);(65.03912516,4.105233677);(67.05477522,2.010505336);(68.99765427,1.006249741);(79.01838972,0.8088820933);(91.01838972,2.284407904);(93.03403978,2.64129018);(95.04968984,3.913163089);(97.0289544,0.7418513661);(107.0496898,2.506473318);(109.0289544,6.11132716);(111.0446045,1.383376555);(117.0340398,0.8892629763);(119.0133043,0.8671466474);(119.0496898,3.441597818);(121.0289544,3.196886549);(123.008219,1.375434873);(133.0289544,3.573804041);(135.008219,1.263501624);(135.0446045,5.124804279);(137.023869,1.895332551);(137.0602545,10.61056705);(139.0395191,2.433732008);(145.0289544,1.200576366);(151.0395191,1.198938235);(163.0395191,15.04200299);(165.0187836,1.53839474);(181.0500838,3.925128444)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(137.05971,65.94);(137.05971,65.94);(137.05971,65.94);(137.05971,65.94);(137.05971,65.94);(137.05971,65.94);(165.05462,66.87);(165.05462,66.87);(165.05462,66.87);(165.05462,66.87);(165.05462,66.87);(165.05462,66.87);(183.06519,20.49);(183.06519,20.49);(183.06519,20.49);(183.06519,20.49)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(55.05423,13.95);(55.05423,13.95);(81.03349,34.86);(81.03349,34.86);(81.03349,34.86);(93.03349,8.58);(93.03349,8.58);(93.03349,8.58);(95.04914,15.71);(95.04914,15.71);(95.04914,15.71);(95.04914,15.71);(109.06479,9.86);(111.04406,11.08);(111.04406,11.08);(111.04406,11.08);(111.04406,11.08);(111.04406,11.08);(119.04914,9.96);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(123.04406,100.0);(135.04406,12.64);(135.04406,12.64);(135.04406,12.64);(135.04406,12.64);(135.04406,12.64);(137.05971,88.14);(137.05971,88.14);(137.05971,88.14);(137.05971,88.14);(137.05971,88.14);(137.05971,88.14);(147.04406,24.77);(147.04406,24.77);(165.05462,30.92);(165.05462,30.92);(165.05462,30.92);(165.05462,30.92);(165.05462,30.92);(165.05462,30.92);(183.06519,15.72);(183.06519,15.72);(183.06519,15.72);(183.06519,15.72)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(39.02293,33.19);(41.03858,11.58);(53.03858,99.26);(55.01784,44.66);(55.05423,15.25);(55.05423,15.25);(65.03858,14.8);(67.01784,19.58);(67.01784,19.58);(67.05423,17.14);(69.03349,17.18);(69.03349,17.18);(79.01784,48.64);(81.03349,100.0);(81.03349,100.0);(81.03349,100.0);(83.04914,14.0);(91.01784,18.44);(91.01784,18.44);(93.03349,33.6);(93.03349,33.6);(93.03349,33.6);(95.04914,90.1);(95.04914,90.1);(95.04914,90.1);(95.04914,90.1);(97.02841,18.44);(107.04914,20.09);(111.04406,20.01);(111.04406,20.01);(111.04406,20.01);(111.04406,20.01);(111.04406,20.01);(113.05971,13.57);(113.05971,13.57);(113.05971,13.57);(113.05971,13.57);(113.05971,13.57);(117.03349,12.64);(119.04914,15.15);(123.04406,36.55);(123.04406,36.55);(123.04406,36.55);(123.04406,36.55);(123.04406,36.55);(123.04406,36.55);(123.04406,36.55);(135.04406,14.75);(135.04406,14.75);(135.04406,14.75);(135.04406,14.75);(135.04406,14.75);(137.05971,24.61);(137.05971,24.61);(137.05971,24.61);(137.05971,24.61);(137.05971,24.61);(137.05971,24.61);(163.03897,12.92)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(163.04007,14.13);(163.04007,14.13);(163.04007,14.13);(181.05063,100.0);(181.05063,100.0);(181.05063,100.0);(181.05063,100.0)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(95.05024,8.35);(95.05024,8.35);(95.05024,8.35);(119.05024,6.96);(135.04515,44.86);(135.04515,44.86);(135.04515,44.86);(135.04515,44.86);(135.04515,44.86);(135.04515,44.86);(137.0608,100.0);(137.0608,100.0);(137.0608,100.0);(137.0608,100.0);(181.05063,7.4);(181.05063,7.4);(181.05063,7.4);(181.05063,7.4)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00329,74.25);(43.01894,14.54);(65.03967,20.99);(68.9982,16.35);(68.9982,16.35);(93.03459,26.41);(93.03459,26.41);(93.03459,26.41);(95.05024,14.4);(95.05024,14.4);(95.05024,14.4);(107.05024,27.33);(109.0295,39.59);(109.0295,39.59);(109.0295,39.59);(109.0295,39.59);(109.06589,46.54);(117.03459,13.91);(119.05024,18.95);(133.0295,26.48);(133.0295,26.48);(133.0295,26.48);(135.04515,100.0);(135.04515,100.0);(135.04515,100.0);(135.04515,100.0);(135.04515,100.0);(135.04515,100.0);(137.0608,38.98);(137.0608,38.98);(137.0608,38.98);(137.0608,38.98)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
5-NonadecylresorcinolCommon wheatCereals and cereal products PublicationsShow
5-NonadecylresorcinolQuinoaPulses and beans PublicationsShow
5-NonadecylresorcinolRyeCereals and cereal products PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
3-(3,5-Dihydroxyphenyl)propanoic acid 3,5-dihydroxycinnamic acidhumanurinehost metabolismNot AvailableNot Available10-30%C9H8O4180.042258738 Publications
3-(3,5-Dihydroxyphenyl)propanoic acid 3,5-dihydroxyphenylethanol glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot Available Publications
3-(3,5-Dihydroxyphenyl)propanoic acid 3,5-dihydroxyphenylethanol sulfatehumanurinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC8H10O6S234.01980921 Publications
5-Nonadecylresorcinol 3-(3,5-Dihydroxyphenyl)propanoic acidhuman mouseplasma (major), urinehost metabolismNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
3-(3,5-Dihydroxyphenyl)propanoic acid 3,5-dihydroxycinnamic acidSexEffect, clusters Publications
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