Cannabis Compound Database: Showing Compound Card for (-)-Menthone (CDB005274)

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Record Information

Version

1.0

Created at

2020-04-17 19:26:46 UTC

Updated at

2020-12-07 19:11:52 UTC

CannabisDB ID

CDB005274

Secondary Accession Numbers

Not 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,4S)-Menthone	ChEBI
(1R,4S)-p-Menthan-3-one	ChEBI
(2S,5R)-2-Isopropyl-5-methylcyclohexanone	ChEBI
(2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone	ChEBI
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone	ChEBI
L-Menthone	ChEBI
p-Menthan-3-one	ChEBI
(2S,5R)-Menthone	ChEBI, HMDB
(-)-(1R,4S)-Menthone	HMDB
(-)-(2S,5R)-Menthone	HMDB
(-)-5-Methyl-2-(1-methylethyl)cyclohexanone	HMDB
(1R,4S)-(-)-P-Menthan-3-one	HMDB
(2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanone	HMDB
(2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanone	HMDB
5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanone	HMDB
5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanone	HMDB
Menthone	MeSH, HMDB
(-)-Menthone	HMDB
(1R,4S)-p-Menth-3-one	HMDB
(2S,5R)-(-)-Menthone	HMDB
(2S,5R)-2-Isopropyl-5-methylcyclohexan-1-one	HMDB
trans-(-)-p-Menthan-3-one	HMDB

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.25

Monoisotopic Molecular Weight

154.1358

IUPAC Name

(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

Traditional Name

(-)-menthone

CAS Registry Number

21060-23-1

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 Key

NFLGAXVYCFJBMK-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

menthone (CHEBI:15410 )
Menthane monoterpenoids (C00843 )
Cyclic monoterpenes (C00843 )
Menthane monoterpenoids (LMPR0102090004 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Role

Industrial application:

Biological role:

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	-6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.5 mg/mL at 25 °C	Not Available
logP	3.05	Not Available

Predicted Properties

Property	Value	Source
logP	2.65	ALOGPS
logP	3.05	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.52 m³·mol⁻¹	ChemAxon
Polarizability	19.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-07bf-9300000000-03e6f833d8a9130c9648	2018-05-25	View Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-03di-7900000000-72f9ad70ae1001e21eaf	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-004j-2900000000-9f3548951fa6e98aa410	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-0170-4900000000-82f88e79cd91a887a98f	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-03di-7900000000-72f9ad70ae1001e21eaf	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-004j-2900000000-9f3548951fa6e98aa410	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-0170-4900000000-82f88e79cd91a887a98f	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	Spectrum
GC-MS	(-)-Menthone, non-derivatized, GC-MS Spectrum	splash10-07bo-9300000000-3f63fc6dbb3efa362d59	Spectrum
Predicted GC-MS	(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052g-9300000000-f26613921d7b53d7fd71	Spectrum
Predicted GC-MS	(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(-)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-6701bba716a6affa8766	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0002-9000000000-b0b5dd86e6d1a6de2171	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-d18a7464317ee5b6d7cc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-244db80c070c100b12b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-2900000000-b84cff8176943c1c01cf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-4900000000-3164f9befc45e23067a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-7900000000-aa7dd74302c4ed215ce5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-001a-9600000000-f847c953bdb697e434a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0012-9400000000-23a0fccfb9523e3d21ec	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9200000000-54afdeb4f58eddee2447	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000t-9100000000-b0e554c807437d6fbe0a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-000t-9000000000-575fad481c43a10742f2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00l2-9000000000-2869717ccfb0fbe67a4b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-015a-9000000000-b2a684427d58a3d1e8d8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0690-9000000000-68fcde55699d18a522f7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0ar3-9100000000-25c9da89880a6d44b24d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9000000000-96ef6ca330f562128056	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-70388bb385562f798a7a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-1900000000-05762909cf77edb47697	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-fa99f8c083212e4f2fc3	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9800000000-7bf975ea31bcef83aa61	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9000000000-3f8923896797c4486693	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d55afdef2faae68197a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-91ec697d11dad181a342	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01oy-9600000000-7933610ac6051fc8ef81	2016-08-03	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0035162

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26447

PDB ID

Not Available

ChEBI ID

15410

References

General References

Not Available

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

Structure for CDB005274 ((-)-Menthone)