metabolite

Showing entry for 5,5'-Dicaffeic acid

Identification

PhytoHub ID
PHUB001147
Name
5,5'-Dicaffeic acid
Systematic Name
Not Available
Synonyms
  • Caffeic acid-5-5-caffeic acid
CAS Number
Not Available
Average Mass
358.302
Monoisotopic Mass
358.068867411
Chemical Formula
C18H14O8
IUPAC Name
(2E)-3-{5'-[(1E)-2-carboxyeth-1-en-1-yl]-2',3',5,6-tetrahydroxy-[1,1'-biphenyl]-3-yl}prop-2-enoic acid
InChI Key
GOQXOMYMZHGINX-ZPUQHVIOSA-N
InChI Identifier
InChI=1S/C18H14O8/c19-13-7-9(1-3-15(21)22)5-11(17(13)25)12-6-10(2-4-16(23)24)8-14(20)18(12)26/h1-8,19-20,25-26H,(H,21,22)(H,23,24)/b3-1+,4-2+
SMILES
OC(=O)\C=C\C1=CC(=C(O)C(O)=C1)C1=C(O)C(O)=CC(\C=C\C(O)=O)=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
3.24e-02 g/l
LogS (ALOGPS)
-4.04
LogP (ALOGPS)
2.89
Hydrogen Acceptors
8
Hydrogen Donors
6
Rotatable Bond Count
5
Polar Surface Area
155.51999999999998
Refractivity
93.12159999999999
Polarizability
35.183329128104674
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-6.323545653963658
pKa (strongest acidic)
3.040625227126632
Number of Rings
2
Rule of Five
No
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
5,5'-Diferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Benzene and substituted derivatives
Super-class
Benzenoids
Sub-class
Biphenols
Direct Parent Name
Biphenols
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Biphenyls and derivatives", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acids", "Coumaric acids and derivatives", "Dicarboxylic acids and derivatives", "Hydrocarbon derivatives", "Hydroxycinnamic acids", "Organic oxides", "Styrenes"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Biphenol", "Biphenyl", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Cinnamic acid", "Cinnamic acid or derivatives", "Coumaric acid or derivatives", "Dicarboxylic acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Hydroxycinnamic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(43.01838972,0.2677366014);(61.0289544,0.4165550617);(71.01330434,1.372028672);(73.0289544,0.256773351);(161.023869,0.8158072982);(163.0395191,0.289267689);(177.0187836,0.3023676368);(179.0344337,1.12904564);(181.0500838,0.4620943014);(255.0657338,0.2631558371);(267.0657338,0.4567296859);(269.0449984,0.3930555957);(271.0606485,0.2676706305);(281.0449984,2.94024232);(285.039913,0.4594413872);(287.0555631,0.8517476491);(289.0712131,0.3274201777);(295.0606485,2.377509366);(297.039913,6.373398645);(297.0762985,0.933441951);(299.0555631,6.458278288);(311.0555631,0.7853357608);(311.0555631,0.2793658762);(313.0712131,5.565260222);(315.0868632,0.5904200691);(323.0555631,2.206686623);(323.0555631,6.993224859);(327.0504777,0.3658547419);(329.0661278,0.3930715875);(341.0661278,19.75434249);(359.0766924,35.65266999)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(71.01330434,3.920946953);(97.0289544,0.7972517584);(133.0289544,2.23087312);(161.023869,1.377742332);(177.0187836,1.797378938);(179.0344337,2.498574318);(181.0500838,0.8264009207);(241.0500838,1.499418439);(255.0657338,2.896053652);(267.0293483,3.086957529);(267.0657338,3.647729587);(269.0813839,0.9975026289);(281.0449984,3.710213153);(283.0242629,3.851752051);(283.0606485,0.9718783987);(285.039913,1.172974443);(287.0555631,1.137767387);(293.0449984,0.7810141082);(295.0606485,4.470499003);(297.039913,9.194420417);(297.0762985,2.52669086);(299.0555631,8.40027319);(311.0555631,1.226056942);(311.0555631,1.338049213);(313.0712131,10.55182805);(315.0868632,1.151491871);(323.0555631,1.778917568);(323.0555631,2.653183203);(329.0661278,2.297976755);(341.0661278,8.24785869);(359.0766924,8.96032452)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,1.372058215);(71.01330434,3.655620471);(95.01330434,1.300919926);(97.0289544,1.057976303);(121.0289544,1.069150953);(133.0289544,2.184859573);(147.0446045,2.085057957);(175.0395191,1.290982651);(191.0344337,1.341023988);(201.0187836,3.379678686);(225.0187836,2.956794621);(229.0500838,2.066142751);(239.0344337,1.480257055);(241.0500838,22.35333166);(243.0657338,4.273705619);(251.0344337,1.777904128);(253.0500838,7.484575591);(255.0657338,9.803153244);(267.0293483,1.448728276);(267.0657338,8.092908622);(269.0449984,1.628590437);(279.0293483,1.187994857);(281.0449984,1.981403006);(283.0242629,1.33774511);(283.0606485,1.161508133);(285.0762985,1.340120686);(297.039913,4.640694402);(299.0555631,2.009703011);(311.0555631,1.09202276);(323.0555631,1.816608642);(327.0504777,1.328778662)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(41.00273965,0.4300892414);(44.99765427,0.15713553);(59.01330434,1.374309547);(61.0289544,0.4229035324);(131.0133043,0.2399452209);(133.0289544,0.5673288169);(135.0446045,0.6449712317);(161.023869,0.3182445255);(175.0031336,0.1631537002);(177.0187836,1.083893866);(179.0344337,4.605490557);(181.0500838,0.2928301988);(219.0293483,0.1479655645);(265.0500838,0.1407864384);(267.0657338,0.3591039852);(269.0813839,0.7333018523);(287.0555631,0.1098678486);(295.0606485,0.5916524322);(297.039913,0.2621577738);(297.039913,0.0915778376);(299.0555631,0.2173105192);(301.0712131,0.0801099523);(309.039913,0.134651264);(311.0555631,0.6962902276);(313.0712131,9.997152156);(315.0504777,0.117082719);(321.039913,0.06625079);(327.0504777,0.141592646);(327.0504777,0.1582304864);(339.0504777,3.855731767);(357.0610424,71.79888777)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(41.00273965,0.9446445132);(44.99765427,1.019611731);(59.01330434,4.743605538);(61.0289544,0.3918127429);(121.0289544,0.3508581009);(131.0133043,1.418427988);(133.0289544,3.897149937);(135.0446045,4.391391208);(161.023869,2.603770031);(163.0395191,0.3619790198);(175.0031336,0.8787983893);(177.0187836,2.642333177);(179.0344337,16.04587672);(181.0500838,0.9818092432);(265.0500838,0.3768462687);(267.0657338,1.436050805);(269.0813839,1.541054388);(295.0242629,0.4852275514);(295.0606485,1.689105731);(297.039913,1.277457408);(297.039913,0.7052660885);(299.0555631,1.270388149);(301.0712131,0.5004729955);(309.039913,0.7286239257);(311.0555631,1.504185278);(313.0712131,10.77409207);(315.0504777,0.6841510675);(325.0348276,0.3123119981);(339.0504777,4.38172034);(341.0297422,0.3585314892);(357.0610424,31.30244611)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,4.635342888);(43.01838972,0.9146480794);(44.99765427,5.753489647);(59.01330434,7.449700356);(61.0289544,2.645375053);(119.0133043,0.8473363458);(121.0289544,1.728138428);(131.0133043,3.34944667);(133.0289544,10.80038897);(135.0446045,8.644915638);(149.023869,0.9118883028);(159.008219,0.7928240193);(161.023869,9.78136261);(163.0395191,1.848194014);(175.0031336,5.039557068);(177.0187836,2.964441133);(179.0344337,11.99439161);(181.0500838,1.507051292);(267.0657338,1.181878032);(269.0449984,1.231398976);(269.0813839,0.9380190607);(295.0242629,0.820831588);(295.0606485,1.530614468);(297.039913,1.212265951);(299.0555631,2.424551515);(313.0712131,1.312718554);(315.0504777,0.8651114601);(325.0348276,0.9585259965);(327.0504777,1.263072955);(339.0504777,3.792346718);(357.0610424,0.8601726011)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
5,5'-Diferulic acidBarleyCereals and cereal products PublicationsShow
5,5'-Diferulic acidCommon wheatCereals and cereal products PublicationsShow
5,5'-Diferulic acidCornCereals and cereal products PublicationsShow
5,5'-Diferulic acidOatCereals and cereal products PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
5,5'-Diferulic acid 5,5'-Dicaffeic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC18H14O8358.068867411 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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