metabolite

Showing entry for Dihydroperillic acid glucuronide (cis-)

Identification

PhytoHub ID
PHUB001003
Name
Dihydroperillic acid glucuronide (cis-)
Systematic Name
Z-p-menth-8-en-7-oic acid glucuronide
Synonyms
Not Available
CAS Number
Not Available
Average Mass
344.36
Monoisotopic Mass
344.147117733
Chemical Formula
C16H24O8
IUPAC Name
4,5,6-trihydroxy-2-[(1r,4r)-4-(prop-1-en-2-yl)cyclohexanecarbonyloxy]oxane-3-carboxylic acid
InChI Key
VHFLDVUTUUPFHN-OCSVBGQESA-N
InChI Identifier
InChI=1S/C16H24O8/c1-7(2)8-3-5-9(6-4-8)14(21)23-16-10(13(19)20)11(17)12(18)15(22)24-16/h8-12,15-18,22H,1,3-6H2,2H3,(H,19,20)/t8-,9-,10?,11?,12?,15?,16?
SMILES
CC(=C)[C@H]1CC[C@@H](CC1)C(=O)OC1OC(O)C(O)C(O)C1C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.81e+01 g/l
LogS (ALOGPS)
-1.28
LogP (ALOGPS)
0.01
Hydrogen Acceptors
7
Hydrogen Donors
4
Rotatable Bond Count
5
Polar Surface Area
133.52
Refractivity
79.6986
Polarizability
34.99995471055118
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.5067815101428494
pKa (strongest acidic)
3.83199102962359
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
Terpenoid metabolites
Class
Monoterpenoid metabolites
Sub-class
Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
LimoneneTerpenoidsMonoterpenoidsNot AvailableShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Monoterpenoids
Direct Parent Name
Menthane monoterpenoids
Alternative Parent Names
["1,2-diols", "Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acid esters", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hemiacetals", "Hydrocarbon derivatives", "Monocyclic monoterpenoids", "Monosaccharides", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1,2-diol", "Acetal", "Alcohol", "Aliphatic heteromonocyclic compound", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Dicarboxylic acid or derivatives", "Hemiacetal", "Hydrocarbon derivative", "Hydroxy acid", "Monocyclic monoterpenoid", "Monosaccharide", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "P-menthane monoterpenoid", "Polyol", "Secondary alcohol"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(83.08607535,0.6668459288);(89.02386902,0.6651702676);(109.0653399,0.763887197);(109.1017254,0.6407224057);(123.1173755,2.693893279);(131.0344337,1.787706179);(133.1017254,0.9726263601);(149.09664,2.460114838);(151.1122901,23.55609707);(153.1279402,0.6497754837);(159.0293483,1.61630659);(161.0449984,0.6805058313);(169.1228548,6.030151453);(177.039913,5.551256962);(195.0504777,0.8506879352);(237.112684,0.9552514338);(267.1232487,1.347677541);(269.1388988,0.9668647667);(281.1388988,2.070990176);(283.1545488,0.6311659308);(287.1130779,0.6699861153);(297.1338134,1.193414458);(299.1494635,6.287467966);(301.1651135,1.302759508);(303.1079926,0.8177730815);(305.1236426,1.11450077);(309.1338134,2.070371107);(313.128728,0.8324490714);(315.1443781,0.9156828059);(327.1443781,13.29414152);(345.1549428,15.94375597)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(67.05477522,0.9731994537);(69.07042529,0.9411785139);(71.01330434,0.8269984804);(81.07042529,1.513440629);(83.04968984,0.8740703502);(83.08607535,1.424387539);(95.08607535,1.373313567);(97.06533991,0.7629284627);(107.0496898,1.197343447);(109.0653399,1.833188185);(109.1017254,0.7559393343);(111.08099,1.01463659);(119.0860754,1.060280821);(123.1173755,4.139087332);(129.0187836,1.092793703);(131.0344337,7.432229353);(133.0500838,1.684637101);(133.1017254,3.1099421);(149.09664,0.8471440002);(151.1122901,27.53548903);(159.0293483,6.013772973);(161.0449984,1.722459071);(169.1228548,6.15408707);(177.039913,10.17182278);(237.112684,1.021250129);(281.1388988,2.130871614);(299.1494635,2.081130782);(301.1651135,1.206413654);(309.1338134,2.181862647);(327.1443781,4.79368082);(345.1549428,2.130420468)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(51.0234751,1.52371765);(53.03912516,3.610793194);(59.01330434,1.833695035);(67.05477522,5.340120241);(69.07042529,2.096065764);(71.01330434,3.197493816);(73.0289544,1.628332315);(81.07042529,3.099349791);(83.04968984,2.836399713);(83.08607535,3.03242108);(87.00821896,3.000881658);(89.02386902,1.697938712);(95.08607535,3.257189715);(97.06533991,2.236571972);(101.023869,2.83403516);(109.1017254,3.550295004);(115.0031336,1.512626754);(117.0187836,2.479057678);(121.1017254,1.701954677);(123.1173755,3.190516735);(125.1330255,2.097717137);(131.0344337,10.49241016);(149.09664,4.009063517);(151.1122901,13.286138);(153.1279402,1.520734924);(159.0293483,2.523927239);(161.0449984,3.351915905);(163.0606485,1.47503784);(177.039913,3.767863495);(237.112684,2.07595482);(281.1388988,1.739780293)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(59.01330434,2.865108056);(75.00821896,0.7155105945);(115.0031336,0.5279619292);(117.0187836,1.16058086);(119.0344337,0.802960337);(123.1173755,2.300789421);(129.0187836,0.5102657493);(131.0344337,0.5838328779);(147.0293483,1.152032247);(149.09664,10.63333359);(167.1072047,1.780787718);(175.0242629,0.8931753376);(191.1072047,1.134796019);(221.1177694,1.946596611);(237.112684,1.400858348);(239.1283341,0.8134246713);(251.1283341,13.19402502);(253.1075986,0.8226086806);(253.1439842,7.903465876);(267.1232487,2.309068626);(269.1388988,0.7505378557);(279.1232487,1.370347672);(281.1388988,1.844716677);(281.1388988,0.7033311012);(283.1181633,1.057900439);(295.1181633,1.200943889);(297.1338134,11.99271125);(299.1494635,14.44669801);(313.128728,0.5378632444);(325.128728,1.746271856);(343.1392927,10.89749544)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(43.01838972,1.109620302);(59.01330434,1.007442915);(73.0289544,2.879778961);(84.99256889,1.207631961);(87.00821896,1.155127721);(103.0031336,0.8259320901);(103.0395191,3.692029481);(123.1173755,3.482302263);(129.0187836,0.8852122154);(131.0344337,7.432528493);(133.0500838,2.300930891);(145.0136983,0.8211718934);(147.0293483,1.491793629);(149.0449984,1.222768529);(149.09664,4.393599677);(167.1072047,12.21025936);(175.0242629,1.071476497);(193.1228548,3.760971269);(207.1021193,1.940260899);(209.1177694,15.98930157);(237.112684,1.5860099);(251.1283341,0.8239397838);(253.1075986,1.807938191);(253.1439842,3.286755906);(255.1232487,0.8194490479);(269.1388988,0.7535849885);(281.1388988,6.947414161);(297.1338134,1.428701659);(299.1494635,11.39069718);(325.128728,1.247062871);(343.1392927,1.028305692)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(15.0234751,1.025321196);(44.99765427,1.057237553);(59.01330434,8.686578795);(61.0289544,2.333802749);(68.99765427,2.361063301);(71.01330434,1.420324);(84.99256889,2.757202358);(87.00821896,3.613082366);(89.02386902,4.692123687);(103.0395191,1.481038283);(115.0031336,3.179512286);(117.0187836,1.292013874);(119.0344337,2.156449714);(123.1173755,7.149953299);(131.0344337,2.37428902);(133.0136983,2.266943844);(147.08099,0.9610474246);(149.09664,10.12082967);(151.1122901,0.994803411);(153.1279402,0.9918374223);(167.1072047,12.93749324);(173.0086129,1.130908711);(175.0242629,1.297931386);(179.1072047,6.841145459);(191.1072047,1.968352464);(193.1228548,3.615148694);(195.1021193,3.62314817);(223.1334195,1.758890864);(237.112684,1.716382046);(239.1283341,2.395639053);(253.1439842,1.799505663)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
LimoneneAppleFruit, Pomes PublicationsShow
LimoneneDillHerbs and SpicesShow
LimoneneGinsengHerbs and Spices PublicationsShow
LimoneneGrapeFruit, Berries PublicationsShow
LimoneneGrape wineBeverages, Alcoholic PublicationsShow
LimoneneLemonFruit, Citrus PublicationsShow
LimoneneMandarin orange (Clementine, Tangerine)Fruit, Citrus PublicationsShow
LimoneneMintHerbs and Spices PublicationsShow
LimoneneNutmegHerbs and SpicesShow
LimoneneOrange juiceBeverages, Non-alcoholic PublicationsShow
LimonenePepperHerbs and SpicesShow
LimonenePeppermintHerbs and Spices PublicationsShow
LimoneneStar aniseHerbs and Spices PublicationsShow
LimoneneSweet orangeFruit, Citrus PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Limonene Dihydroperillic acid glucuronide (cis-)humanurineNot AvailableNot AvailableNot AvailableNot AvailableC16H24O8344.147117733 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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