precursor

Showing entry for 1,3-Dicaffeoylquinic acid

Identification

PhytoHub ID
PHUB000512
Name
1,3-Dicaffeoylquinic acid
Systematic Name
Not Available
Synonyms
  • 1,3-O-Dicaffeoylquinic acid
  • Cynarin
CAS Number
30964-13-7
Average Mass
516.455
Monoisotopic Mass
516.126776213
Chemical Formula
C25H24O12
IUPAC Name
1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
InChI Key
YDDUMTOHNYZQPO-FCXRPNKRSA-N
InChI Identifier
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+
SMILES
OC1CC(CC(OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C1O)(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.37e-01 g/l
LogS (ALOGPS)
-3.58
LogP (ALOGPS)
2.07
Hydrogen Acceptors
10
Hydrogen Donors
7
Rotatable Bond Count
9
Polar Surface Area
211.27999999999997
Refractivity
126.76419999999997
Polarizability
49.82347179942785
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.23256292481747
pKa (strongest acidic)
3.184533116763618
Number of Rings
3
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Organooxygen compounds
Super-class
Organic oxygen compounds
Sub-class
Alcohols and polyols
Direct Parent Name
Quinic acids and derivatives
Alternative Parent Names
["1,2-diols", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acid esters", "Coumaric acids and derivatives", "Cyclohexanols", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Organic oxides", "Styrenes", "Tricarboxylic acids and derivatives"]
External Descriptor Annotations
Not Available
Substituent Names
["1,2-diol", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Alpha,beta-unsaturated carboxylic ester", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechol", "Cinnamic acid ester", "Cinnamic acid or derivatives", "Coumaric acid or derivatives", "Cyclohexanol", "Enoate ester", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Hydroxycinnamic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Phenol", "Quinic acid", "Secondary alcohol", "Styrene", "Tricarboxylic acid or derivatives"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(109.0289544,0.8895323859);(123.0446045,1.824158011);(125.0602545,1.5818953);(135.0446045,0.7629560279);(157.0500838,0.6209948602);(159.0657338,0.7314059847);(161.023869,1.517785232);(163.0395191,14.22651345);(173.0449984,0.7382090701);(175.0606485,1.569781148);(181.0500838,0.6326205285);(191.0555631,0.6423509528);(291.0868632,1.794649493);(307.0817778,1.108754635);(319.0817778,3.601156364);(321.0974279,1.409706052);(335.0766924,1.692783779);(337.0923425,13.27120834);(339.1079926,1.862128391);(349.055957,0.7746198474);(355.1029072,8.130450751);(391.0665217,0.7489371105);(393.0821717,1.023630789);(395.0978218,2.154020518);(407.0978218,1.681739045);(471.1291219,0.7020912472);(481.1134719,1.913371134);(487.1240366,1.20450687);(499.1240366,12.19287214);(499.1240366,0.9410585806);(517.1346012,18.05411197)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(109.0289544,1.45730682);(123.0446045,4.206983632);(133.0289544,1.524260584);(135.0446045,4.203384993);(161.023869,1.178789136);(163.0395191,19.62176707);(175.0606485,2.634310947);(177.0762985,1.101848534);(191.0555631,3.353977856);(193.0712131,2.121215821);(291.0868632,1.473308712);(307.0817778,2.578189095);(309.0974279,1.723338952);(311.1130779,1.359694384);(319.0817778,2.488370208);(321.0974279,1.140760687);(325.0923425,1.674283781);(337.0923425,13.15111863);(339.1079926,2.712158298);(355.1029072,7.551944374);(373.055957,0.9510176431);(391.0665217,1.076655483);(393.0821717,1.941999656);(405.0821717,0.931260618);(407.0978218,2.933249616);(471.1291219,1.657168053);(473.144772,1.042649586);(481.1134719,2.325725521);(487.1240366,3.171084559);(499.1240366,4.472184137);(517.1346012,2.239992608)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(105.0340398,2.104947758);(107.0496898,1.810591881);(109.0289544,3.128793743);(123.0446045,4.852639167);(133.0289544,2.002203014);(135.0446045,3.061117569);(159.0657338,2.081203306);(163.0395191,10.90727959);(171.0293483,2.282945047);(173.0449984,3.816844182);(175.0606485,11.31395193);(177.0762985,1.536328437);(191.0555631,8.62868414);(193.0500838,2.736419629);(203.0344337,1.613635751);(291.0868632,5.383433848);(307.0817778,2.355392384);(311.0766924,1.679852135);(321.0974279,1.630570882);(329.0297422,1.737632788);(337.0923425,4.988407659);(341.1236426,1.63852754);(395.0978218,1.950939012);(403.0665217,1.646193941);(405.0821717,1.631685046);(407.0978218,2.475427234);(429.0821717,1.548462992);(455.0978218,2.161816826);(457.1134719,3.488378133);(487.1240366,2.028005792);(499.1240366,1.77768865)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(121.0289544,0.3577071213);(123.0446045,0.4019301779);(135.0446045,1.429884835);(161.023869,5.861708166);(177.0187836,0.5043996989);(179.0344337,8.795400046);(189.039913,0.3735840028);(249.039913,2.322420098);(251.0555631,0.3985445743);(291.0504777,0.3947298889);(291.0868632,0.680143997);(305.0661278,0.4756857633);(307.0817778,1.9584158);(309.0974279,2.27698938);(323.0766924,0.62249636);(335.0766924,7.385561409);(351.0716071,0.3158660322);(353.0872571,16.87575916);(391.0665217,0.4224719698);(393.0821717,0.8487345097);(409.0923425,0.3246050675);(453.1185573,0.4568717356);(453.1185573,2.160884704);(455.0978218,1.082597554);(457.1134719,0.6494013515);(469.1134719,1.460861658);(471.1291219,9.162885874);(483.0927364,0.3964903);(485.1083865,1.461353484);(497.1083865,3.452611358);(515.1189512,26.68900392)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(121.0289544,5.234265411);(123.0446045,1.568924016);(135.0446045,2.38931215);(157.0500838,1.121535658);(161.023869,6.30849975);(173.0449984,3.021365027);(175.0606485,1.439801442);(179.0344337,11.16701644);(231.0504777,2.062146117);(263.0555631,2.268396854);(265.0712131,2.15221904);(291.0868632,4.680198397);(293.1025133,1.849908443);(305.0661278,1.325287119);(307.0817778,5.919087584);(309.0974279,6.141049227);(323.0766924,1.369004013);(335.0766924,6.720065171);(337.0923425,1.76436365);(349.0923425,1.55925556);(353.0872571,8.792034895);(379.0665217,1.044741951);(381.0821717,1.115255368);(391.0665217,1.101275509);(393.0821717,2.163186285);(453.1185573,1.605069503);(453.1185573,1.704797749);(469.1134719,1.354186615);(471.1291219,5.045495198);(497.1083865,2.515788994);(515.1189512,3.496466862)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,1.487361972);(71.01330434,0.7316514209);(121.0289544,1.043396493);(133.0289544,1.399502193);(135.0446045,2.854656461);(143.0133043,0.9205707322);(159.008219,0.9320626462);(161.023869,13.36635788);(163.0395191,1.067033807);(173.0449984,0.7093130791);(179.0344337,24.12482283);(189.0187836,0.9365347206);(189.039913,5.772544039);(191.0555631,3.471150625);(193.0712131,0.7989009017);(205.0500838,1.071463179);(217.0348276,1.362952975);(217.0500838,0.8422207693);(229.0348276,2.059320247);(231.0504777,3.989213345);(291.0868632,0.7780785097);(305.0661278,1.580775473);(307.0817778,12.79754795);(309.0974279,6.697729349);(323.0766924,0.7747168708);(335.0766924,2.813256986);(337.0923425,1.541719867);(349.0923425,0.8455521108);(353.0872571,1.151507199);(379.0665217,0.9602994953);(381.0821717,1.117785875)

Food Sources

NameGroup
Globe artichokeVegetables, Other vegetables PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
1,3-Dicaffeoylquinic acid 1,5-Diferuloylquinic acidhumanplasmahost-gut microbiota co-metabolite3h-5h20-50 nmol/LNot Available Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Back