PhytoHub: Showing entry for 3-Feruloylquinic acid

3-Feruloylquinic acid

Identification

PhytoHub ID

PHUB000531

Name

3-Feruloylquinic acid

Systematic Name

3- Feruloylquinic acid

Synonyms

Not Available

CAS Number

87099-72-7

Average Mass

368.338

Monoisotopic Mass

368.110732224

Chemical Formula

C₁₇H₂₀O₉

IUPAC Name

1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

InChI Key

RAGZUCNPTLULOL-HWKANZROSA-N

InChI Identifier

InChI=1S/C17H20O9/c1-25-12-6-9(2-4-10(12)18)3-5-14(20)26-13-8-17(24,16(22)23)7-11(19)15(13)21/h2-6,11,13,15,18-19,21,24H,7-8H2,1H3,(H,22,23)/b5-3+

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC2CC(O)(CC(O)C2O)C(O)=O)=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 3.04e+00 g/l
LogS (ALOGPS): -2.08
LogP (ALOGPS): 0.23
Hydrogen Acceptors: 8
Hydrogen Donors: 5
Rotatable Bond Count: 6
Polar Surface Area: 153.74999999999997
Refractivity: 87.71700000000001
Polarizability: 35.393016073505976
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -3.2318239809154075
pKa (strongest acidic): 3.3306011433051217
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PeakForestCompound: 000428

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Phenolic acids
Sub-class: Hydroxycinnamic acids

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Globe artichoke (Poly)phenols	Polyphenols	Not specified	Not specified	Show Food Phytochemical
3-Feruloylquinic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical

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-hydroxy-2-unsubstituted benzenoids", "Alkyl aryl ethers", "Alpha hydroxy acids and derivatives", "Anisoles", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acid esters", "Coumaric acids and derivatives", "Cyclohexanols", "Dicarboxylic acids and derivatives", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Organic oxides", "Phenoxy compounds", "Polyols", "Styrenes", "Tertiary alcohols"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "Alkyl aryl ether", "Alpha,beta-unsaturated carboxylic ester", "Alpha-hydroxy acid", "Anisole", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Cinnamic acid ester", "Cinnamic acid or derivatives", "Coumaric acid or derivatives", "Cyclohexanol", "Dicarboxylic acid or derivatives", "Enoate ester", "Ether", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Hydroxy acid", "Hydroxycinnamic acid or derivatives", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Organic oxide", "Phenol", "Phenol ether", "Phenoxy compound", "Polyol", "Quinic acid", "Secondary alcohol", "Styrene", "Tertiary alcohol"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(127.0395191,0.6287558158);(129.0551691,3.280328327);(131.0708192,1.233150301);(137.0602545,1.85741578);(139.0759046,1.576058002);(145.0500838,1.675400943);(147.0657338,1.157928848);(149.0602545,0.7721671036);(155.0344337,0.5526890724);(157.0500838,1.849453291);(159.0657338,0.8802104757);(173.0449984,1.218776257);(175.0395191,1.655863403);(175.0606485,7.988778342);(177.0551691,13.55079244);(177.0762985,0.9795595144);(193.0712131,4.609369774);(195.0657338,0.7121722765);(219.0657338,0.6192998143);(221.0813839,0.5646983166);(233.0661278,0.8620271392);(305.1025133,4.037218261);(307.1181633,0.7230581293);(321.0974279,1.437895497);(323.1130779,10.52002801);(325.128728,1.348623776);(333.0974279,1.670624538);(337.0923425,0.7232870035);(339.1079926,0.8871255915);(351.1079926,11.46007919);(369.1185573,18.96716477)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(129.0551691,3.027988583);(131.0708192,1.2593084);(137.0602545,4.557505686);(145.0289544,1.581110179);(145.0500838,4.307501971);(147.0446045,1.910383453);(147.0657338,2.845061693);(149.0602545,4.460062493);(149.0813839,2.207478679);(157.0500838,3.010837463);(159.0657338,0.9423346559);(173.0449984,0.8370630923);(175.0395191,1.453779583);(175.0606485,12.53633866);(177.0551691,18.78567694);(177.0762985,1.582232019);(193.0712131,6.585351374);(199.0606485,0.9380573037);(229.0348276,0.8805464571);(245.0661278,0.7598206862);(291.0868632,0.6036485626);(293.1025133,0.914854242);(305.1025133,3.589014115);(307.1181633,0.9068697237);(323.1130779,4.255359286);(325.128728,0.7940266002);(333.0974279,3.052321112);(337.0923425,1.068132553);(339.1079926,1.25777422);(351.1079926,5.765640479);(369.1185573,3.323919734)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(43.01838972,3.804774703);(79.01838972,2.330766038);(89.02386902,1.233902775);(105.0340398,1.305363651);(107.0496898,2.251549459);(115.0395191,3.564965514);(117.0551691,1.858550691);(123.0446045,2.444894536);(129.0551691,7.491214209);(131.0708192,1.414022194);(135.0446045,1.238340345);(137.0602545,4.664180592);(145.0289544,3.117330937);(145.0500838,9.83830364);(147.0446045,2.107318876);(147.0657338,3.856359865);(149.0602545,3.693643752);(155.0344337,1.21598934);(157.0500838,2.7856695);(159.0657338,2.756739172);(161.023869,1.694710317);(173.0449984,2.561466212);(175.0395191,2.442151776);(175.0606485,12.07824519);(177.0551691,8.476524259);(187.0606485,1.409910538);(199.0606485,1.87941459);(207.0657338,1.322361514);(217.0500838,1.348353755);(263.0919486,1.68542923);(305.1025133,2.127552828)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(87.00821896,3.05005148);(129.0551691,0.3493516407);(135.0446045,0.3257841177);(137.0602545,0.402691578);(143.0344337,0.3977452395);(145.0500838,1.546219328);(147.0657338,1.537905299);(149.0602545,1.28672722);(161.0449984,0.3382907774);(173.0449984,3.163133195);(175.0395191,5.45901986);(177.0187836,0.7453427421);(191.0344337,0.4853594201);(191.0555631,8.697232469);(193.0500838,7.787300058);(219.0657338,0.5639862358);(231.0504777,0.4212721479);(261.0762985,0.7329433422);(291.0868632,0.4367996714);(293.0661278,0.2920539934);(293.1025133,0.6848891741);(305.1025133,6.086953378);(307.0817778,0.975872328);(307.0817778,1.64719726);(321.0974279,2.750816221);(323.1130779,17.83271351);(335.0766924,0.5566042517);(337.0923425,1.668837502);(349.0923425,3.332391108);(351.0716071,0.3014971319);(367.1029072,26.14301832)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,1.49826448);(57.03403978,1.116752169);(73.0289544,1.258471105);(87.00821896,2.765063756);(103.0395191,2.323225454);(129.0551691,4.231956531);(131.0708192,1.31186241);(135.0446045,5.749719355);(137.0602545,1.51943361);(143.0344337,1.609630222);(145.0500838,5.363089163);(147.0657338,5.296372614);(149.0602545,1.706409752);(173.0449984,4.381223954);(175.0395191,6.024095022);(177.0187836,2.129296748);(187.0606485,1.421613276);(191.0555631,6.471284863);(193.0500838,7.040245298);(219.0657338,0.8951073759);(229.0348276,0.9390683659);(231.0504777,1.528367095);(279.0868632,1.756819512);(293.1025133,1.886449762);(305.1025133,5.463746861);(307.0817778,4.781296429);(321.0974279,2.882186932);(323.1130779,8.079293054);(337.0923425,0.9492385712);(349.0923425,3.054395543);(367.1029072,4.566020719)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,0.9368049771);(43.01838972,1.270997781);(71.01330434,0.8628163858);(73.0289544,1.718134469);(87.00821896,0.7989021487);(103.0395191,2.599539189);(129.0551691,1.905966676);(133.0289544,1.951630739);(143.0344337,4.281625567);(145.0289544,1.818289129);(145.0500838,19.29782452);(147.0446045,0.9274018535);(147.0657338,12.10487401);(149.0602545,1.242491244);(159.008219,1.270800415);(161.023869,2.453378438);(161.0449984,0.8602501793);(163.0395191,1.485821177);(173.0449984,3.246267695);(175.0395191,7.643579677);(177.0187836,7.201880176);(177.0551691,1.414774376);(185.0449984,2.095022473);(187.0606485,2.034473846);(191.0344337,0.953152979);(191.0555631,3.805279239);(193.0500838,8.957075561);(293.1025133,0.794065808);(305.1025133,0.8070373262);(307.0817778,2.417731782);(335.0766924,0.8421101636)

Food Sources

	Name	Group
	Apricot	Fruit, Drupes	Publications	Show
	Coffee	Coffee and coffee products	Publications	Show

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	3-Feruloylquinic acid	Apricot	Fruit, Drupes	Publications	Show
	3-Feruloylquinic acid	Coffee	Coffee and coffee products	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	3-Feruloylquinic acid		3-Feruloylquinic acid	human	plasma, urine	unchanged	<1h	<20 nmol/L	1-5%	C₁₇H₂₀O₉	368.110732224	Detailed Intervention Studies	Publications
	Globe artichoke (Poly)phenols		3-Feruloylquinic acid	human	plasma, urine	host metabolism	1h-3h	20-50 nmol/L	<1%	C₁₇H₂₀O₉	368.110732224	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	3-Feruloylquinic acid		3-Feruloylquinic acid	Microbiota	Effect, clusters	Publications
	Globe artichoke (Poly)phenols		3-Feruloylquinic acid	Microbiota	Effect, clusters	Publications

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Showing entry for 3-Feruloylquinic acid