PhytoHub: Showing entry for Dihydroperillic acid glucuronide (trans-)

Dihydroperillic acid glucuronide (trans-)

Identification

PhytoHub ID

PHUB001002

Name

Dihydroperillic acid glucuronide (trans-)

Systematic Name

E-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

3,4,5-trihydroxy-6-[(1s,4s)-4-(prop-1-en-2-yl)cyclohexanecarbonyloxy]oxane-2-carboxylic acid

InChI Key

SOFCHPTZCVYNEZ-GBZOVYLJSA-N

InChI Identifier

InChI=1S/C16H24O8/c1-7(2)8-3-5-9(6-4-8)15(22)24-16-12(19)10(17)11(18)13(23-16)14(20)21/h8-13,16-19H,1,3-6H2,2H3,(H,20,21)/t8-,9+,10?,11?,12?,13?,16?

SMILES

CC(=C)[C@H]1CC[C@H](CC1)C(=O)OC1OC(C(O)C(O)C1O)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.82e+01 g/l
LogS (ALOGPS): -1.28
LogP (ALOGPS): 0.00
Hydrogen Acceptors: 7
Hydrogen Donors: 4
Rotatable Bond Count: 5
Polar Surface Area: 133.52
Refractivity: 79.62019999999998
Polarizability: 34.540194374844354
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -3.6868986916885658
pKa (strongest acidic): 3.4382814121157828
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Metabolite

Family: Terpenoid metabolites
Class: Monoterpenoid metabolites
Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Limonene	Terpenoids	Monoterpenoids	Not Available	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Prenol lipids
Super-class: Lipids and lipid-like molecules
Sub-class: Terpene glycosides
Direct Parent Name: Terpene glycosides
Alternative Parent Names: ["Acetals", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acid esters", "Carboxylic acids", "Dicarboxylic acids and derivatives", "Hydrocarbon derivatives", "Menthane monoterpenoids", "Monocyclic monoterpenoids", "Monosaccharides", "O-glucuronides", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Polyols", "Pyrans", "Secondary alcohols"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-o-glucuronide", "Acetal", "Alcohol", "Aliphatic heteromonocyclic compound", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Dicarboxylic acid or derivatives", "Glucuronic acid or derivatives", "Hydrocarbon derivative", "Hydroxy acid", "Monocyclic monoterpenoid", "Monosaccharide", "Monoterpenoid", "O-glucuronide", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "P-menthane monoterpenoid", "Polyol", "Pyran", "Secondary alcohol", "Terpene glycoside"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(83.08607535,0.6439207313);(99.00821896,0.4945621015);(109.0653399,0.6156562775);(109.1017254,0.6036060863);(117.0187836,0.5815076857);(121.1017254,0.4842236929);(123.1173755,3.757278358);(125.0602545,0.8098461921);(125.1330255,0.4820712823);(127.0759046,1.490694152);(129.0915547,0.4070379757);(133.1017254,0.7838899862);(149.09664,2.030024014);(151.1122901,20.88911318);(153.1279402,0.5032241067);(159.0293483,3.375548394);(161.0449984,1.20124751);(165.0915547,0.8745839018);(167.1072047,0.5342504306);(169.1228548,23.2440119);(173.0086129,0.4822126199);(173.1541549,0.5570854399);(175.0242629,1.139227644);(177.039913,8.652366485);(179.0555631,0.6280501355);(181.0712131,0.4910927618);(195.0504777,0.7074404648);(305.1236426,0.6768036638);(309.1338134,1.829094404);(327.1443781,10.04425748);(345.1549428,10.98607093)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(43.01838972,0.7619226192);(67.05477522,1.088855907);(69.07042529,1.07150648);(81.07042529,1.253823164);(83.08607535,1.674784408);(87.04460446,0.8751875437);(95.08607535,1.414087293);(107.0496898,1.067811687);(109.0653399,1.634869071);(109.1017254,0.8399502071);(111.08099,0.9048705376);(119.0860754,1.26787374);(121.1017254,0.8865758054);(123.1173755,7.977344454);(125.0602545,1.116985704);(125.1330255,1.243770554);(127.0759046,1.974342404);(129.0915547,2.044993129);(131.0344337,1.02979402);(133.1017254,2.773500393);(149.09664,1.154617019);(151.1122901,27.47134748);(159.0293483,5.289755978);(161.0449984,0.9518675649);(167.1072047,0.7785907641);(169.1228548,16.38474863);(177.039913,6.777809889);(299.1494635,0.9309854255);(309.1338134,1.813734937);(327.1443781,3.784641706);(345.1549428,1.75905149)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(43.01838972,2.166836472);(51.0234751,1.467994019);(53.03912516,2.269348983);(67.05477522,5.576471539);(69.07042529,2.49624518);(81.07042529,3.030139009);(83.04968984,1.369351621);(83.08607535,3.556447105);(87.00821896,4.536440902);(87.04460446,2.231533482);(89.02386902,3.016492434);(91.03951908,1.399308738);(93.07042529,2.123428707);(95.08607535,6.177072086);(97.10172542,1.562268511);(101.0602545,2.688016125);(105.0187836,1.826551685);(109.1017254,4.728746971);(117.0187836,3.86100956);(121.1017254,2.572929613);(123.1173755,6.84907696);(125.1330255,2.706674978);(131.0344337,2.227139311);(149.09664,2.968190117);(151.1122901,11.29270834);(159.0293483,2.746801785);(161.0449984,3.236779594);(163.0606485,1.90368943);(169.1228548,3.93969329);(177.039913,2.011739512);(193.0864693,1.460873943)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(41.00273965,1.052137279);(56.99765427,0.4845686417);(59.01330434,0.7396174644);(71.01330434,1.830011701);(73.0289544,0.5714459246);(87.00821896,1.299969547);(89.02386902,1.976820082);(101.023869,0.4766147116);(103.0031336,1.283926884);(117.0187836,1.957292878);(123.1173755,5.369105028);(131.0344337,0.6142834546);(147.0293483,1.493469897);(147.08099,0.4298388964);(149.0449984,0.4224981618);(149.09664,14.23400313);(163.0242629,0.9226954366);(165.0915547,0.5345106058);(167.1072047,25.62099496);(175.0242629,3.582446954);(193.0348276,0.7000404189);(209.1177694,0.932735624);(225.112684,0.5282539671);(239.1283341,0.4483921741);(269.1388988,0.4011628798);(281.1388988,1.775921906);(297.1338134,2.385318008);(299.1494635,5.342915925);(313.128728,0.5131841631);(325.128728,2.820712257);(343.1392927,19.25511104)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,2.753572182);(56.99765427,0.7579480932);(59.01330434,2.304353028);(71.01330434,1.229043425);(72.99256889,0.9945690572);(73.0289544,4.692557591);(87.00821896,1.868106729);(89.02386902,2.025038828);(103.0395191,1.826124159);(117.0187836,0.8508920999);(121.1017254,0.786090377);(123.1173755,12.93799653);(129.0187836,0.9632611811);(131.0344337,4.754421452);(133.0500838,1.401656613);(145.0136983,0.9108015724);(147.0293483,1.501283954);(149.0449984,1.153622274);(149.09664,6.080855028);(167.1072047,27.12031833);(175.0242629,6.516161192);(179.1072047,1.034151702);(193.0348276,1.728570621);(209.1177694,0.9621509258);(225.112684,0.8413048146);(281.1388988,1.954109767);(297.1338134,1.347787321);(299.1494635,2.907873715);(325.128728,2.334501238);(325.128728,0.8298668961);(343.1392927,2.631009301)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,5.825884263);(43.01838972,7.90821281);(44.99765427,0.7913474368);(56.99765427,1.866704657);(59.01330434,8.047846981);(61.0289544,5.713695556);(71.01330434,2.422532288);(72.99256889,0.6118503322);(73.0289544,3.849257566);(84.99256889,0.6861018344);(87.00821896,1.356867556);(89.02386902,1.527715004);(91.03951908,0.9595463529);(101.023869,0.8491414798);(103.0395191,2.491558626);(117.0187836,0.6538865325);(119.0344337,0.6112219448);(119.0860754,1.131276105);(121.1017254,1.410802402);(123.1173755,9.976379618);(129.0187836,1.493393743);(131.0344337,8.40934499);(133.0500838,1.543842956);(147.0293483,1.649802336);(149.0449984,1.0119675);(149.09664,6.088546627);(151.1122901,0.7495625751);(165.0915547,0.5929471879);(167.1072047,17.95239211);(175.0242629,0.8608252515);(207.1021193,0.9555453727)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Limonene	Apple	Fruit, Pomes	Publications	Show
Limonene	Dill	Herbs and Spices		Show
Limonene	Ginseng	Herbs and Spices	Publications	Show
Limonene	Grape	Fruit, Berries	Publications	Show
Limonene	Grape wine	Beverages, Alcoholic	Publications	Show
Limonene	Lemon	Fruit, Citrus	Publications	Show
Limonene	Mandarin orange (Clementine, Tangerine)	Fruit, Citrus	Publications	Show
Limonene	Mint	Herbs and Spices	Publications	Show
Limonene	Nutmeg	Herbs and Spices		Show
Limonene	Orange juice	Beverages, Non-alcoholic	Publications	Show
Limonene	Pepper	Herbs and Spices		Show
Limonene	Peppermint	Herbs and Spices	Publications	Show
Limonene	Star anise	Herbs and Spices	Publications	Show
Limonene	Sweet orange	Fruit, Citrus	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
	Limonene		Dihydroperillic acid glucuronide (trans-)	human mouse	urine	Not Available	Not Available	Not Available	Not Available	C₁₆H₂₄O₈	344.147117733		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Dihydroperillic acid glucuronide (trans-)