NP-MRD: Showing NP-Card for (+)-menthone (NP0297936)

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Record Information

Version

2.0

Created at

2022-09-10 08:44:20 UTC

Updated at

2022-09-10 08:44:20 UTC

NP-MRD ID

NP0297936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-menthone

Description

(+)-Menthone, also known as (1S,4R)-menthone or D-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. A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2R,5S-stereoisomer) (+)-Menthone is an extremely weak basic (essentially neutral) compound (based on its pKa) (+)-Menthone is a minty tasting compound. Outside of the human body, (+)-Menthone has been detected, but not quantified in, herbs and spices. (+)-menthone is found in Achillea abrotanoides, Agastache foeniculum, Agathosma betulina, Artemisia dracunculus, Betonica macrantha, Clinopodium arkansanum, Clinopodium brownei, Clinopodium carolinianum, Clinopodium serpyllifolium, Clinopodium suaveolens, Cyclotrichium niveum, Cymbopogon citratus, Hedeoma multiflora, Hedyosmum mexicanum, Hesperozygis rhododon, Hyssopus seravschanicus, Lavandula stoechas, Lepechinia chamaedryoides, Mentha aquatica, Mentha arvensis, Mentha piperita, Mentha pulegium, Mentha rotundifolia, Mentha canadensis, Mentha verticillata, Minthostachys andina, Minthostachys verticillata, Pelargonium graveolens, Pelargonium tomentosum, Pistacia vera, Plagiochila rutilans, Platostoma africanum, Poliomintha incana, Polygala senega, Pycnanthemum floridanum, Rhanterium epapposum, Senna alexandrina, Swertia japonica and Xylopia aromatica. This could make (+)-menthone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.0327   -0.0830    0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351    0.2780   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331   -0.8542   -1.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7569    0.6275    0.2538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1026   -0.5040    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530   -0.0698    1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232   -0.2803   -0.1424 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5339   -0.2250   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979    0.7499   -1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1087    1.1707   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    2.0518   -1.5156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.9366    1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1398    0.8143    1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -0.3728    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5731    1.1801   -0.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -0.5203   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7278   -1.7686   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1794   -1.0009   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.4522    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791   -1.4305    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -0.7484    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    1.0130    1.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -0.6446    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.3066   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -0.9485    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593   -0.5705   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    0.7946    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5653    0.4702   -2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1562    1.6623   -0.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  4 10  1  0
 10 11  2  0
 10  9  1  0
  9  7  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  8 27  1  0
  6 22  1  0
  6 23  1  0
  5 20  1  0
  5 21  1  0
  4 19  1  1
  2 15  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  9 28  1  0
  9 29  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1    2    9                                                  
CONECT    8    3    4    6   12                                             
CONECT    9    5    7   10   13                                             
CONECT   10    6    9   11                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
(1S,4R)-Menthone	ChEBI
(1S,4R)-p-Menthan-3-one	ChEBI
(2R,5S)-2-Isopropyl-5-methylcyclohexanone	ChEBI
(+)-(1S,4R)-Menthone	HMDB
(2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexanone	HMDB
Menthone	HMDB
(2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanone	HMDB
D-Menthone	HMDB
(+)-Menthone	HMDB

Chemical Formula

C₁₀H₁₈O

Average Mass

154.2493 Da

Monoisotopic Mass

154.13577 Da

IUPAC Name

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

Traditional Name

(+)-menthone

CAS Registry Number

Not Available

SMILES

[H][C@]1(C)CC[C@]([H])(C(C)C)C(=O)C1

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 Key

NFLGAXVYCFJBMK-DTWKUNHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea abrotanoides	LOTUS Database	35616633
Agastache foeniculum	LOTUS Database	35616633
Agathosma betulina	LOTUS Database	35616633
Artemisia dracunculus	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Clinopodium arkansanum	LOTUS Database	35616633
Clinopodium brownei	LOTUS Database	35616633
Clinopodium carolinianum	LOTUS Database	35616633
Clinopodium serpyllifolium	LOTUS Database	35616633
Clinopodium suaveolens	LOTUS Database	35616633
Cyclotrichium niveum	LOTUS Database	35616633
Cymbopogon citratus	LOTUS Database	35616633
Hedeoma multiflora	LOTUS Database	35616633
Hedyosmum mexicanum	LOTUS Database	35616633
Hesperozygis rhododon	LOTUS Database	35616633
Hyssopus seravschanicus	LOTUS Database	35616633
Lavandula stoechas	LOTUS Database	35616633
Lepechinia chamaedryoides	LOTUS Database	35616633
Mentha aquatica	LOTUS Database	35616633
Mentha arvensis	LOTUS Database	35616633
Mentha piperita	LOTUS Database	35616633
Mentha pulegium	LOTUS Database	35616633
Mentha rotundifolia	LOTUS Database	35616633
Mentha sachalinensis	LOTUS Database	35616633
Mentha verticillata	LOTUS Database	35616633
Minthostachys andina	LOTUS Database	35616633
Minthostachys verticillata	LOTUS Database	35616633
Pelargonium graveolens	LOTUS Database	35616633
Pelargonium tomentosum	LOTUS Database	35616633
Pistacia vera	LOTUS Database	35616633
Plagiochila rutilans	LOTUS Database	35616633
Platostoma africanum	LOTUS Database	35616633
Poliomintha incana	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Pycnanthemum floridanum	LOTUS Database	35616633
Rhanterium epapposum	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Xylopia aromatica	LOTUS Database	35616633

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:31 )
Menthane monoterpenoids (C11390 )
Cyclic monoterpenes (C11390 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.05	ChemAxon
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	18.94 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

External Links

HMDB ID

HMDB0035783

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

443159

PDB ID

Not Available

ChEBI ID

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (+)-menthone (NP0297936)

MOL for NP0297936 ((+)-menthone)

3D MOL for NP0297936 ((+)-menthone)

3D SDF for NP0297936 ((+)-menthone)

3D-SDF for NP0297936 ((+)-menthone)

PDB for NP0297936 ((+)-menthone)

3D PDB for NP0297936 ((+)-menthone)

SMILES for NP0297936 ((+)-menthone)

INCHI for NP0297936 ((+)-menthone)

Structure for NP0297936 ((+)-menthone)

3D Structure for NP0297936 ((+)-menthone)