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Showing NP-Card for menthone (NP0213256)

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Record Information
Version2.0
Created at2022-09-05 12:11:39 UTC
Updated at2022-09-05 12:11:39 UTC
NP-MRD IDNP0213256
Secondary Accession NumbersNone
Natural Product Identification
Common Namementhone
DescriptionP-Menthan-3-one, also known as trans-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 found in Achillea abrotanoides, Agastache foeniculum, Artemisia dracunculus, Betonica macrantha, Clinopodium brownei, Clinopodium carolinianum, Clinopodium douglasii, Clinopodium gilliesii, Clinopodium glabrum, Clinopodium serpyllifolium, Clinopodium suaveolens, Cryptomeria japonica, Cyclotrichium niveum, Cymbopogon citratus, Hedeoma multiflora, Hedyosmum mexicanum, Hesperozygis rhododon, Hyssopus seravschanicus, Lavandula stoechas, Lepechinia chamaedryoides, Mentha aquatica, Mentha arvensis, Mentha longifolia, Mentha piperita, Mentha pulegium, Mentha canadensis, Mentha verticillata, Minthostachys andina, Minthostachys mollis, Minthostachys verticillata, Pelargonium graveolens, Pelargonium quercifolium, Pelargonium tomentosum, Pistacia vera, Plagiochila rutilans, Platostoma africanum, Poliomintha incana, Polygala senega, Pycnanthemum floridanum, Rhanterium epapposum, Rhodiola rosea, Schizonepeta tenuifolia, Senna alexandrina, Swertia japonica, Thymus longicaulis and Xylopia aromatica. P-Menthan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0213256 (menthone)


  Mrv1652305221920252D          

 11 11  0  0  0  0            999 V2000
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
Download

3D MOL for NP0213256 (menthone)

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5957   -0.6928   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059   -0.0519    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647    1.2023    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217    0.0893    0.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0429   -1.2728    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276   -1.0482    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101   -0.2127   -0.7221 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5771    0.0002   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248    1.1491   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487    0.9472   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422    1.5097   -1.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -0.1354   -2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -0.6634   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307   -1.7696   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -0.7693    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030    1.7050    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632    1.8979   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274    0.9412    0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    0.4973    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684   -1.7125   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -1.9287    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -0.5153    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817   -1.9997    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -0.7010   -1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068    0.2076    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    0.8732   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -0.9455   -0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170    1.6669    0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.7320   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
M  END
Download

3D SDF for NP0213256 (menthone)


  Mrv1652305221920252D          

 11 11  0  0  0  0            999 V2000
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0213256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC(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

> <INCHI_KEY>
NFLGAXVYCFJBMK-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.024394221277845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2-(propan-2-yl)cyclohexan-1-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.0497874006666668

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.420780675838815

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
46.5201

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-menthan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0213256 (menthone)

Download
PDB for NP0213256 (menthone)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-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
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                                                  
CONECT    9    5    7   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0213256 (menthone)
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SMILES for NP0213256 (menthone)
CC(C)C1CCC(C)CC1=O
Download
INCHI for NP0213256 (menthone)
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
(2R,5S)-Rel-5-methyl-2-(1-methylethyl)cyclohexanoneChEBI
Rel-(1R,4S)-p-menthan-3-oneChEBI
Rel-(2R,5S)-2-isopropyl-5-methylcyclohexanoneChEBI
trans-5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
trans-Menthan-3-oneChEBI
trans-MenthoneChEBI
trans-p-Menthan-3-oneChEBI
2-Isopropyl-5-methylcyclohexanoneChEBI
5-Methyl-2-(1-methylethyl)cyclohexanoneChEBI
5-Methyl-2-(isopropyl)cyclohexanoneChEBI
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Namep-menthan-3-one
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(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
InChI KeyNFLGAXVYCFJBMK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea abrotanoidesLOTUS Database
Agastache foeniculumLOTUS Database
Artemisia dracunculusLOTUS Database
Betonica macranthaLOTUS Database
Clinopodium browneiLOTUS Database
Clinopodium carolinianumLOTUS Database
Clinopodium douglasiiLOTUS Database
Clinopodium gilliesiiLOTUS Database
Clinopodium glabrumLOTUS Database
Clinopodium serpyllifoliumLOTUS Database
Clinopodium suaveolensLOTUS Database
Cryptomeria japonicaLOTUS Database
Cyclotrichium niveumLOTUS Database
Cymbopogon citratusLOTUS Database
Hedeoma multifloraLOTUS Database
Hedyosmum mexicanumLOTUS Database
Hesperozygis rhododonLOTUS Database
Hyssopus seravschanicusLOTUS Database
Lavandula stoechasLOTUS Database
Lepechinia chamaedryoidesLOTUS Database
Mentha aquaticaLOTUS Database
Mentha arvensisLOTUS Database
Mentha longifoliaLOTUS Database
Mentha piperitaLOTUS Database
Mentha pulegiumLOTUS Database
Mentha sachalinensisLOTUS Database
Mentha verticillataLOTUS Database
Minthostachys andinaLOTUS Database
Minthostachys mollisLOTUS Database
Minthostachys verticillataLOTUS Database
Pelargonium graveolensLOTUS Database
Pelargonium quercifoliumLOTUS Database
Pelargonium tomentosumLOTUS Database
Pistacia veraLOTUS Database
Plagiochila rutilansLOTUS Database
Platostoma africanumLOTUS Database
Poliomintha incanaLOTUS Database
Polygala senegaLOTUS Database
Pycnanthemum floridanumLOTUS Database
Rhanterium epapposumLOTUS Database
Rhodiola roseaLOTUS Database
Schizonepeta tenuifoliaLOTUS Database
Senna alexandrinaLOTUS Database
Swertia japonicaLOTUS Database
Thymus longicaulisLOTUS Database
Xylopia aromaticaLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029689  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6986  
PDB IDNot Available
ChEBI ID36503  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]