precursor

Showing entry for 5,5'-Diferulic acid

Identification

PhytoHub ID
PHUB000600
Name
5,5'-Diferulic acid
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
386.356
Monoisotopic Mass
386.10016754
Chemical Formula
C20H18O8
IUPAC Name
(2E)-3-{5'-[(1E)-2-carboxyeth-1-en-1-yl]-2',6-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-yl}prop-2-enoic acid
InChI Key
LBQZVWQOPFFQJI-GGWOSOGESA-N
InChI Identifier
InChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+
SMILES
COC1=C(O)C(=CC(\C=C\C(O)=O)=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.12e-02 g/l
LogS (ALOGPS)
-4.54
LogP (ALOGPS)
2.99
Hydrogen Acceptors
8
Hydrogen Donors
4
Rotatable Bond Count
7
Polar Surface Area
133.52
Refractivity
102.08619999999996
Polarizability
39.0865438121662
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-4.596798124256282
pKa (strongest acidic)
3.113179165520272
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Benzene and substituted derivatives
Super-class
Benzenoids
Sub-class
Biphenyls and derivatives
Direct Parent Name
Biphenyls and derivatives
Alternative Parent Names
["Alkyl aryl ethers", "Anisoles", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids and derivatives", "Dicarboxylic acids and derivatives", "Hydrocarbon derivatives", "Hydroxycinnamic acids", "Methoxybenzenes", "Methoxyphenols", "Organic oxides", "Phenoxy compounds", "Styrenes"]
External Descriptor Annotations
["Neolignans", "ferulic acid"]
Substituent Names
["Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Biphenyl", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Cinnamic acid or derivatives", "Coumaric acid or derivatives", "Dicarboxylic acid or derivatives", "Ether", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Hydroxycinnamic acid or derivatives", "Methoxybenzene", "Methoxyphenol", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenol ether", "Phenoxy compound", "Styrene"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(43.01838972,0.2785128144);(55.01838972,0.2274918575);(61.0289544,0.4822894215);(71.01330434,1.403070469);(73.0289544,0.2916587158);(175.0395191,0.8810725617);(177.0551691,0.3146812527);(193.0500838,1.227326023);(195.0657338,0.5040194273);(283.097034,0.2892564771);(295.097034,0.4719733488);(297.0762985,0.4496300559);(299.0919486,0.2530386023);(309.0762985,3.083649979);(313.0712131,0.5354114946);(315.0868632,0.9012809898);(317.1025133,0.3719036581);(323.0919486,2.502099594);(325.1075986,0.9642430873);(327.0868632,6.875446531);(337.0712131,0.2493688109);(337.0712131,0.2393629891);(339.0868632,0.7691763617);(339.0868632,0.5315836327);(341.1025133,5.913926239);(343.1181633,0.6170455883);(351.0868632,9.228218178);(353.0661278,0.2492951573);(355.0817778,0.702919465);(369.0974279,20.73342655);(387.1079926,38.45762067)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(71.01330434,3.896740206);(151.0395191,1.127973013);(175.0395191,1.704767068);(177.0551691,0.8171692715);(193.0500838,3.038068167);(195.0657338,1.044962208);(269.0813839,1.74794044);(283.097034,3.472211678);(295.097034,3.754839721);(297.0762985,1.255371909);(297.112684,1.034297437);(309.0762985,4.583046935);(309.0762985,1.473530477);(311.0919486,2.7568567);(313.0712131,1.508210022);(315.0868632,1.256174592);(321.0762985,0.7912784113);(323.0919486,4.721756091);(325.1075986,2.517173626);(327.0868632,10.31411254);(337.0712131,1.650515973);(337.0712131,1.563942565);(339.0868632,0.9398771873);(339.0868632,3.021859298);(341.1025133,11.71417456);(343.1181633,1.217401604);(351.0868632,4.076231433);(355.0817778,1.616863241);(357.0974279,1.880700343);(369.0974279,8.921465693);(387.1079926,10.58048758)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,1.800322265);(51.0234751,1.27423019);(71.01330434,3.228750553);(95.01330434,1.599468706);(149.0602545,1.127573865);(161.0602545,2.608008097);(177.0551691,0.9541828081);(189.0551691,1.145424051);(191.0344337,1.104304312);(205.0500838,1.763651788);(217.0500838,1.114531846);(241.0500838,1.663488627);(255.0657338,4.446703276);(267.0657338,1.855591177);(269.0813839,15.16204256);(271.097034,1.767704834);(283.097034,15.22276339);(295.0606485,0.9974546359);(295.097034,11.19371394);(297.039913,0.9279976788);(297.0762985,5.214391449);(297.112684,1.669650658);(299.0919486,1.076901551);(309.0762985,4.440214262);(309.0762985,2.286959461);(311.0919486,1.297245711);(323.0919486,2.775623244);(325.0712131,3.071801076);(327.0868632,4.278261725);(339.0868632,1.677774929);(341.1025133,1.253267338)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(31.01838972,0.2385614134);(41.00273965,0.3076457376);(44.99765427,0.1553423086);(55.01838972,0.2214353218);(59.01330434,1.364397075);(147.0446045,0.4845450785);(149.0602545,0.5354019033);(151.0395191,0.2002643764);(153.0551691,0.1179347229);(175.0395191,0.2485724867);(177.0187836,0.3789993262);(191.0344337,1.05073352);(193.0500838,4.368015403);(275.0555631,0.3946799115);(289.0712131,0.1660695482);(295.097034,0.2985631902);(297.112684,0.5947212922);(309.0762985,0.0947903983);(311.0919486,0.0981859107);(315.0868632,0.1094208775);(323.0919486,0.5058810895);(325.0712131,0.2659679511);(325.0712131,1.422585838);(337.0712131,0.13980527);(339.0868632,0.7227784178);(341.1025133,9.166794769);(353.0661278,0.372639117);(355.0817778,0.341873659);(367.0817778,3.558589923);(369.0610424,0.7310601471);(385.0923425,71.34374402)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(41.00273965,0.8247651624);(44.99765427,0.9456623879);(59.01330434,4.564058071);(147.0446045,2.62528714);(149.0602545,2.549702208);(161.023869,0.8579034119);(163.0395191,0.4731616734);(175.0395191,1.54458791);(177.0187836,4.983379768);(191.0344337,2.408050635);(193.0500838,13.12039283);(295.097034,1.000898169);(297.112684,0.8868455416);(309.0762985,0.5268360565);(311.0555631,1.015646096);(311.0919486,0.4989502104);(313.0712131,0.5405785462);(323.0919486,1.14741405);(325.0712131,1.419311178);(325.0712131,5.848456499);(327.0504777,0.5305087369);(329.0661278,0.5771215062);(337.0712131,0.819454305);(339.0504777,0.4705557729);(339.0868632,1.702924002);(341.1025133,8.697481123);(353.0661278,1.255871056);(355.0817778,0.9222584621);(367.0817778,3.635068111);(369.0610424,4.432992088);(385.0923425,29.1738773)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,3.921253111);(44.99765427,3.656864169);(59.01330434,7.210475834);(147.008219,1.824959498);(147.0446045,5.651938181);(149.0602545,3.356001241);(161.023869,4.085869102);(163.0395191,1.340790124);(173.023869,1.345599258);(175.0031336,1.468316368);(175.0395191,3.603380155);(177.0187836,14.89239777);(191.0344337,2.325582561);(193.0500838,11.56809302);(295.0606485,1.751758826);(295.097034,1.182194366);(297.039913,1.386623245);(311.0555631,1.923411765);(323.0919486,1.108649639);(325.0712131,7.106956265);(327.0504777,1.251402947);(329.0661278,1.809470661);(337.0712131,1.350902516);(337.0712131,1.447092208);(337.0712131,1.447092208);(339.0504777,1.875806721);(339.0504777,2.664938163);(353.0661278,1.83966909);(355.0817778,1.134271657);(367.0817778,2.217657901);(369.0610424,2.250581429)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(337.07066,46.2);(337.07066,46.2);(337.07066,46.2);(337.07066,46.2);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(341.10196,23.1);(351.08631,24.85);(351.08631,24.85);(351.08631,24.85);(351.08631,24.85);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(387.10744,14.93);(387.10744,14.93);(387.10744,14.93);(387.10744,14.93);(387.10744,14.93);(387.10744,14.93);(387.10744,14.93)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(177.05462,6.22);(295.0601,8.27);(295.0601,8.27);(295.0601,8.27);(309.07575,17.53);(309.07575,17.53);(309.07575,17.53);(323.0914,27.71);(323.0914,27.71);(323.0914,27.71);(325.07066,9.84);(325.07066,9.84);(325.07066,9.84);(325.07066,9.84);(325.07066,9.84);(325.07066,9.84);(325.10705,14.21);(325.10705,14.21);(325.10705,14.21);(327.08631,21.76);(327.08631,21.76);(327.08631,21.76);(327.08631,21.76);(327.08631,21.76);(327.08631,21.76);(337.07066,47.7);(337.07066,47.7);(337.07066,47.7);(337.07066,47.7);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(341.10196,40.42);(351.08631,43.08);(351.08631,43.08);(351.08631,43.08);(351.08631,43.08);(355.08123,5.88);(355.08123,5.88);(359.11253,7.4);(359.11253,7.4);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(369.09688,100.0);(387.10744,61.13);(387.10744,61.13);(387.10744,61.13);(387.10744,61.13);(387.10744,61.13);(387.10744,61.13);(387.10744,61.13)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(57.03349,17.07);(149.05971,24.62);(267.06519,19.42);(271.09649,44.96);(293.04445,22.56);(293.10196,16.45);(293.10196,16.45);(295.09649,60.23);(297.07575,23.86);(297.07575,23.86);(297.07575,23.86);(297.07575,23.86);(297.07575,23.86);(297.07575,23.86);(297.11214,96.3);(299.0914,20.43);(299.0914,20.43);(299.0914,20.43);(307.0601,31.81);(307.0601,31.81);(307.0601,31.81);(309.07575,40.84);(309.07575,40.84);(309.07575,40.84);(311.05501,15.85);(311.05501,15.85);(311.0914,37.23);(311.0914,37.23);(311.0914,37.23);(311.0914,37.23);(313.07066,33.83);(313.07066,33.83);(313.10705,43.67);(313.10705,43.67);(313.10705,43.67);(313.10705,43.67);(315.08631,45.13);(315.08631,45.13);(323.0914,54.23);(323.0914,54.23);(323.0914,54.23);(325.07066,30.76);(325.07066,30.76);(325.07066,30.76);(325.07066,30.76);(325.07066,30.76);(325.07066,30.76);(325.10705,66.9);(325.10705,66.9);(325.10705,66.9);(327.08631,51.41);(327.08631,51.41);(327.08631,51.41);(327.08631,51.41);(327.08631,51.41);(327.08631,51.41);(337.07066,23.45);(337.07066,23.45);(337.07066,23.45);(337.07066,23.45);(339.08631,23.06);(339.08631,23.06);(339.08631,23.06);(339.08631,23.06);(339.08631,23.06);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(341.10196,100.0);(343.11761,23.01);(343.11761,23.01);(343.11761,23.01);(343.11761,23.01);(343.11761,23.01);(343.11761,23.01);(351.08631,24.59);(351.08631,24.59);(351.08631,24.59);(351.08631,24.59);(355.08123,27.1);(355.08123,27.1);(357.09688,28.8);(357.09688,28.8);(367.08123,19.87);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78);(369.09688,43.78)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(295.09758,90.31);(297.11323,55.48);(325.07176,88.56);(325.07176,88.56);(325.07176,88.56);(325.07176,88.56);(325.07176,88.56);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(341.10306,65.64);(385.09289,100.0);(385.09289,100.0);(385.09289,100.0);(385.09289,100.0);(385.09289,100.0);(385.09289,100.0)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(295.09758,100.0);(297.11323,50.72);(309.07685,13.67);(309.07685,13.67);(309.07685,13.67);(309.07685,13.67);(325.07176,71.08);(325.07176,71.08);(325.07176,71.08);(325.07176,71.08);(325.07176,71.08)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(95.05024,6.09);(121.0295,5.85);(149.0608,6.9);(201.05572,6.88);(203.07137,5.92);(233.04555,6.96);(233.04555,6.96);(255.06628,9.14);(255.06628,9.14);(267.06628,9.96);(267.06628,9.96);(267.06628,9.96);(269.08193,31.15);(269.08193,31.15);(269.08193,31.15);(271.09758,9.69);(271.09758,9.69);(271.09758,9.69);(285.07685,11.9);(285.07685,11.9);(295.09758,58.14);(297.11323,26.95);(299.05611,11.77);(299.05611,11.77);(299.05611,11.77);(299.05611,11.77);(301.07176,7.7);(309.07685,6.16);(309.07685,6.16);(309.07685,6.16);(309.07685,6.16);(311.0925,25.13);(311.0925,25.13);(311.0925,25.13);(311.0925,25.13);(313.10815,10.76);(313.10815,10.76);(313.10815,10.76);(323.05611,9.35);(323.0925,12.02);(323.0925,12.02);(325.07176,100.0);(325.07176,100.0);(325.07176,100.0);(325.07176,100.0);(325.07176,100.0);(339.05103,6.62);(339.08741,8.13);(339.08741,8.13);(339.08741,8.13);(339.08741,8.13);(355.08233,10.16);(355.08233,10.16);(383.07724,42.89);(383.07724,42.89);(383.07724,42.89)

Food Sources

NameGroup
BarleyCereals and cereal products PublicationsShow
Common wheatCereals and cereal products PublicationsShow
CornCereals and cereal products PublicationsShow
OatCereals 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
5,5'-Diferulic acid 5,5'-Dihydroferulic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC20H22O8390.131467668 Publications
5,5'-Diferulic acid Caffeic acid-5-5-dihydrocaffeic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC18H16O8360.084517475 Publications
5,5'-Diferulic acid Ferulic acid-5-5-caffeic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC19H16O8372.084517475 Publications
5,5'-Diferulic acid Ferulic acid-5-5-dihydroferulic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC20H20O8388.115817604 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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