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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:54:24 UTC
Update Date2021-10-13 06:44:50 UTC
HMDB IDHMDB0034972
Secondary Accession Numbers
  • HMDB0059864
  • HMDB34972
  • HMDB59864
Metabolite Identification
Common NameIsomenthone
DescriptionIsomenthone 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. Based on a literature review a small amount of articles have been published on Isomenthone.
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
IsomenthoneMeSH
(-)-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
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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point205.00 to 208.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility180.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.625 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP10(2.65) g/LALOGPS
logP10(3.05) g/LChemAxon
logS10(-2.8) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.96631661259
DarkChem[M-H]-132.15531661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isomenthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r7-9300000000-1d150f2cf0a23dbfef0b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomenthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 10V, Positive-QTOFsplash10-0a4i-0900000000-fa99f8c083212e4f2fc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 20V, Positive-QTOFsplash10-0bt9-9800000000-7bf975ea31bcef83aa612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 40V, Positive-QTOFsplash10-0aor-9000000000-3f8923896797c44866932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 10V, Negative-QTOFsplash10-0udi-0900000000-d55afdef2faae68197a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 20V, Negative-QTOFsplash10-0udi-0900000000-91ec697d11dad181a3422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 40V, Negative-QTOFsplash10-01oy-9600000000-7933610ac6051fc8ef812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 20V, Negative-QTOFsplash10-0udi-0900000000-084e13e285859f435a612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 40V, Negative-QTOFsplash10-0gbc-9700000000-57929498deae48afce7a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 10V, Positive-QTOFsplash10-0bti-3900000000-5b9ac9ca9aaff729e2d12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 20V, Positive-QTOFsplash10-0532-9200000000-ac0243da1ad4aa3d859e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomenthone 40V, Positive-QTOFsplash10-0006-9000000000-d3a7bbb5abb9a0381a392021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1507821
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.