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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:06:32 UTC
Update Date2022-03-07 02:54:23 UTC
HMDB IDHMDB0035162
Secondary Accession Numbers
  • HMDB35162
Metabolite Identification
Common Name(-)-Menthone
Description(-)-Menthone, also known as (1R,4S)-menthone or L-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. (-)-Menthone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule.
Structure
Data?1563862676
Synonyms
ValueSource
(1R,4S)-MenthoneChEBI
(1R,4S)-p-Menthan-3-oneChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanoneChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
L-MenthoneChEBI
p-Menthan-3-oneChEBI
(2S,5R)-MenthoneChEBI, HMDB
(-)-(1R,4S)-MenthoneHMDB
(-)-(2S,5R)-MenthoneHMDB
(-)-5-Methyl-2-(1-methylethyl)cyclohexanoneHMDB
(1R,4S)-(-)-P-Menthan-3-oneHMDB
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanoneHMDB
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanoneHMDB
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanoneHMDB
MenthoneMeSH, HMDB
(-)-MenthoneHMDB
(1R,4S)-p-Menth-3-oneHMDB
(2S,5R)-(-)-MenthoneHMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-oneHMDB
trans-(-)-p-Menthan-3-oneHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name(-)-menthone
CAS Registry Number14073-97-3
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+/m1/s1
InChI KeyNFLGAXVYCFJBMK-BDAKNGLRSA-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

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-6 °CNot Available
Boiling Point207.00 to 210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.5 mg/mL at 25 °CNot Available
LogP3.05Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability19.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.98131661259
DarkChem[M-H]-133.22431661259
DeepCCS[M+H]+135.38630932474
DeepCCS[M-H]-132.65430932474
DeepCCS[M-2H]-168.43330932474
DeepCCS[M+Na]+143.64230932474
AllCCS[M+H]+133.532859911
AllCCS[M+H-H2O]+129.132859911
AllCCS[M+NH4]+137.632859911
AllCCS[M+Na]+138.832859911
AllCCS[M-H]-140.032859911
AllCCS[M+Na-2H]-141.632859911
AllCCS[M+HCOO]-143.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-MenthoneCC(C)[C@@H]1CC[C@@H](C)CC1=O1485.7Standard polar33892256
(-)-MenthoneCC(C)[C@@H]1CC[C@@H](C)CC1=O1142.9Standard non polar33892256
(-)-MenthoneCC(C)[C@@H]1CC[C@@H](C)CC1=O1146.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Menthone,1TMS,isomer #1CC(C)C1=C(O[Si](C)(C)C)C[C@H](C)CC11342.3Semi standard non polar33892256
(-)-Menthone,1TMS,isomer #1CC(C)C1=C(O[Si](C)(C)C)C[C@H](C)CC11360.6Standard non polar33892256
(-)-Menthone,1TMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C=C1O[Si](C)(C)C1290.0Semi standard non polar33892256
(-)-Menthone,1TMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C=C1O[Si](C)(C)C1346.5Standard non polar33892256
(-)-Menthone,1TBDMS,isomer #1CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](C)CC11565.8Semi standard non polar33892256
(-)-Menthone,1TBDMS,isomer #1CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@H](C)CC11544.0Standard non polar33892256
(-)-Menthone,1TBDMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C1493.2Semi standard non polar33892256
(-)-Menthone,1TBDMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C1503.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (-)-Menthone EI-B (Non-derivatized)splash10-03di-7900000000-72f9ad70ae1001e21eaf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone GC-EI-TOF (Non-derivatized)splash10-004j-2900000000-9f3548951fa6e98aa4102017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone GC-EI-TOF (Non-derivatized)splash10-0170-4900000000-82f88e79cd91a887a98f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone EI-B (Non-derivatized)splash10-03di-7900000000-72f9ad70ae1001e21eaf2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone GC-EI-TOF (Non-derivatized)splash10-004j-2900000000-9f3548951fa6e98aa4102018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone GC-EI-TOF (Non-derivatized)splash10-0170-4900000000-82f88e79cd91a887a98f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone EI-B (Non-derivatized)splash10-07bo-9300000000-3f63fc6dbb3efa362d592018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Menthone EI-B (Non-derivatized)splash10-07bo-9300000000-3f63fc6dbb3efa362d592018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Menthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9300000000-f26613921d7b53d7fd712016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Menthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Menthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-07bf-9300000000-03e6f833d8a9130c96482018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone n/a 10V, positive-QTOFsplash10-014i-9000000000-6701bba716a6affa87662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone n/a 10V, positive-QTOFsplash10-0002-9000000000-b0b5dd86e6d1a6de21712020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone n/a 10V, positive-QTOFsplash10-000t-9000000000-d18a7464317ee5b6d7cc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 1V, positive-QTOFsplash10-000i-1900000000-244db80c070c100b12b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 1V, positive-QTOFsplash10-000i-2900000000-b84cff8176943c1c01cf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 2V, positive-QTOFsplash10-000i-4900000000-3164f9befc45e23067a92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 2V, positive-QTOFsplash10-000i-7900000000-aa7dd74302c4ed215ce52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 3V, positive-QTOFsplash10-001a-9600000000-f847c953bdb697e434a92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 3V, positive-QTOFsplash10-0012-9400000000-23a0fccfb9523e3d21ec2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 4V, positive-QTOFsplash10-000t-9200000000-54afdeb4f58eddee24472020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 4V, positive-QTOFsplash10-000t-9100000000-b0e554c807437d6fbe0a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 6V, positive-QTOFsplash10-000t-9000000000-575fad481c43a10742f22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 7V, positive-QTOFsplash10-00l2-9000000000-2869717ccfb0fbe67a4b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 9V, positive-QTOFsplash10-015a-9000000000-b2a684427d58a3d1e8d82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 10V, positive-QTOFsplash10-0690-9000000000-68fcde55699d18a522f72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 13V, positive-QTOFsplash10-0ar3-9100000000-25c9da89880a6d44b24d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone n/a 10V, positive-QTOFsplash10-000t-9000000000-96ef6ca330f5621280562020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone n/a 10V, positive-QTOFsplash10-014i-9000000000-70388bb385562f798a7a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Menthone Orbitrap 0V, positive-QTOFsplash10-0a4i-1900000000-05762909cf77edb476972020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 10V, Positive-QTOFsplash10-0a4i-0900000000-fa99f8c083212e4f2fc32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 20V, Positive-QTOFsplash10-0bt9-9800000000-7bf975ea31bcef83aa612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 40V, Positive-QTOFsplash10-0aor-9000000000-3f8923896797c44866932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 10V, Negative-QTOFsplash10-0udi-0900000000-d55afdef2faae68197a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 20V, Negative-QTOFsplash10-0udi-0900000000-91ec697d11dad181a3422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Menthone 40V, Negative-QTOFsplash10-01oy-9600000000-7933610ac6051fc8ef812016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB009778
KNApSAcK IDC00000811
Chemspider ID24636
KEGG Compound IDC00843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26447
PDB IDNot Available
ChEBI ID15410
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008131
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.