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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:19:06 UTC
Update Date2018-05-19 23:11:20 UTC
HMDB IDHMDB0060004
Secondary Accession Numbers
  • HMDB60004
Metabolite Identification
Common NameMenthol-glucoronide
DescriptionMenthol-glucuronide is a metabolite of menthol in urine. Menthol is extensively metabolized such that excretion in the urine is predominantly menthol glucuronide. Urine menthol is a Biomarker of mentholated cigarette Smoking, as detected in methol cigarette smokers. (PMID: 20962297 )
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H28O6
Average Molecular Weight316.3899
Monoisotopic Molecular Weight316.188588628
IUPAC Name(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[5-methyl-2-(propan-2-yl)cyclohexyl]oxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(2-isopropyl-5-methylcyclohexyl)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(C)CC1[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C16H28O6/c1-7(2)9-5-4-8(3)6-10(9)14-12(18)11(17)13(19)15(22-14)16(20)21/h7-15,17-19H,4-6H2,1-3H3,(H,20,21)/t8?,9?,10?,11-,12-,13+,14+,15+/m1/s1
InChI KeyJOHLBVHVVBAEGN-GEPIISMBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • C-glucuronide
  • Glucuronic acid or derivatives
  • C-glycosyl compound
  • Glycosyl compound
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • P-menthane monoterpenoid
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.97 g/LALOGPS
logP0.93ALOGPS
logP1.23ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.42 m³·mol⁻¹ChemAxon
Polarizability34.09 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08gi-3890000000-c199de16023237c4d1b6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-3201490000-263a8fd901ef01da0e25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0396000000-a9806541eb6b0031238aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfs-5961000000-90b42a323d785b98ce82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9710000000-d421313a96efd147f3ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2379000000-cb7fe618ec05c02d0a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-8492000000-e97faed618d6c10a075dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053f-9810000000-70b55459a128ac23c3d7View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID89620
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]
  2. Benowitz NL, Dains KM, Dempsey D, Havel C, Wilson M, Jacob P 3rd: Urine menthol as a biomarker of mentholated cigarette smoking. Cancer Epidemiol Biomarkers Prev. 2010 Dec;19(12):3013-9. doi: 10.1158/1055-9965.EPI-10-0706. Epub 2010 Oct 20. [PubMed:20962297 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.