Showing Compound Card for (-)-Menthone (CDB005274)

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Record Information
Version1.0
Created at2020-04-17 19:26:46 UTC
Updated at2020-12-07 19:11:52 UTC
CannabisDB IDCDB005274
Secondary Accession NumbersNot Available
Cannabis Compound 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. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule (-)-Menthone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (-)-Menthone is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name(-)-menthone
CAS Registry Number21060-23-1
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

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point-6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mL at 25 °CNot Available
logP3.05Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-07bf-9300000000-03e6f833d8a9130c96482018-05-25View Spectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-72f9ad70ae1001e21eafSpectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-004j-2900000000-9f3548951fa6e98aa410Spectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-0170-4900000000-82f88e79cd91a887a98fSpectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
GC-MS(-)-Menthone, non-derivatized, GC-MS Spectrumsplash10-07bo-9300000000-3f63fc6dbb3efa362d59Spectrum
Predicted GC-MS(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052g-9300000000-f26613921d7b53d7fd71Spectrum
Predicted GC-MS(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-6701bba716a6affa87662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0002-9000000000-b0b5dd86e6d1a6de21712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-d18a7464317ee5b6d7cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-244db80c070c100b12b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-2900000000-b84cff8176943c1c01cf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-4900000000-3164f9befc45e23067a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-7900000000-aa7dd74302c4ed215ce52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9600000000-f847c953bdb697e434a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9400000000-23a0fccfb9523e3d21ec2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-54afdeb4f58eddee24472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9100000000-b0e554c807437d6fbe0a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-575fad481c43a10742f22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-2869717ccfb0fbe67a4b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-015a-9000000000-b2a684427d58a3d1e8d82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0690-9000000000-68fcde55699d18a522f72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0ar3-9100000000-25c9da89880a6d44b24d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-96ef6ca330f5621280562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-70388bb385562f798a7a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-1900000000-05762909cf77edb476972020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fa99f8c083212e4f2fc32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9800000000-7bf975ea31bcef83aa612016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-3f8923896797c44866932016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d55afdef2faae68197a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-91ec697d11dad181a3422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9600000000-7933610ac6051fc8ef812016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035162
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available