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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:54:24 UTC
Update Date2020-06-15 17:04:53 UTC
HMDB IDHMDB0034972
Secondary Accession Numbers
  • HMDB0059864
  • HMDB34972
  • HMDB59864
Metabolite Identification
Common NameIsomenthone
DescriptionIsomenthone, also known as alpha-isomenthone or cis-p-menthone, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Isomenthone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862644
Synonyms
ValueSource
(1S,4S)-(-)-p-Menthan-3-oneChEBI
(1S,4S)-p-Menthan-3-oneChEBI
(2S,5S)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S-cis)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-IsomenthoneChEBI
(1R,4R)-(+)-p-Menthan-3-oneHMDB
(1R,4R)-p-Menthan-3-oneHMDB
(-)-IsomenthoneHMDB
(1S,4S)-IsomenthoneHMDB
(2S,5S)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
(2S,5S)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
alpha-IsomenthoneHMDB
cis-MenthoneHMDB
cis-p-Menthan-3-oneHMDB
cis-p-MenthoneHMDB
DL-IsomenthoneHMDB
Α-isomenthoneHMDB
IsomenthoneMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name(-)-isomenthone
CAS Registry Number18309-28-9
SMILES
CC(C)[C@@H]1CC[C@H](C)CC1=O
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9-/m0/s1
InChI KeyNFLGAXVYCFJBMK-IUCAKERBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.26 g/LALOGPS
logP2.65ALOGPS
logP3.05ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.52 m³·mol⁻¹ChemAxon
Polarizability18.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r7-9300000000-1d150f2cf0a23dbfef0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c4486693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a342Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef81Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014639
KNApSAcK IDC00010904 C00037333
Chemspider ID4937714
KEGG Compound IDC17125
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenthone
METLIN IDNot Available
PubChem Compound6432469
PDB IDNot Available
ChEBI ID36496
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.