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Showing NP-Card for (+-)-pulegone (NP0158515)

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Record Information
Version2.0
Created at2022-09-02 16:07:27 UTC
Updated at2022-09-02 16:07:27 UTC
NP-MRD IDNP0158515
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+-)-pulegone
Description(R)-p-Menth-4(8)-en-3-one, also known as (+-)-pulegone or isopulegone, 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. (+-)-pulegone is found in Mentha aquatica, Mentha gattefossei, Mentha piperita, Mentha pulegium, Mentha canadensis, Mentha spicata, Monarda fistulosa, Poliomintha incana, Pycnanthemum muticum, Schizonepeta multifida and Schizonepeta tenuifolia. (+-)-pulegone was first documented in 2014 (PMID: 24506214). The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (R)-p-Menth-4(8)-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0158515 ((+-)-pulegone)


  Mrv1652305221920262D          

 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  2  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 NP0158515 ((+-)-pulegone)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    2.8954   -1.1235   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1274   -0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8094    1.4054   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    0.0968   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0944   -1.1592   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229   -1.2424   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796    0.0197   -0.6608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4379   -0.0690    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001    1.2490   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    1.3080   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4811    2.3633   -0.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9640   -0.8635   -0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.6275    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -1.7849   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    1.8012   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9152    1.2600   -0.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107    2.1303    0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2495   -1.4130    0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713   -1.9605   -0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -1.8338   -1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431   -1.8747    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2980    0.2456   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746    0.0251   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5281   -1.1001    0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112    0.6236    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4873    1.2505    0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    2.1461   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  4 10  1  0
 10 11  2  0
 10  9  1  0
  9  7  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  7 22  1  6
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  9 26  1  0
  9 27  1  0
M  END
Download

3D SDF for NP0158515 ((+-)-pulegone)


  Mrv1652305221920262D          

 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  2  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>
NP0158515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(=C(C)C)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3

> <INCHI_KEY>
NZGWDASTMWDZIW-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.340993612404013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.8565172766666667

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.434595837136952

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.1294

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-pulegone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0158515 ((+-)-pulegone)

Download
PDB for NP0158515 ((+-)-pulegone)
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 NP0158515 ((+-)-pulegone)
Download
SMILES for NP0158515 ((+-)-pulegone)
CC1CCC(=C(C)C)C(=O)C1
Download
INCHI for NP0158515 ((+-)-pulegone)
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
(+-)-PulegoneChEBI
1-Isopropylidene-4-methyl-2-cyclohexanoneChEBI
1-Methyl-4-isopropylidene-3-cyclohexanoneChEBI
4(8)-p-Menthen-3-oneChEBI
5-Methyl-2-(1-methylethylidene)cyclohexanoneChEBI
5-Methyl-2-isopropylidenecyclohexanoneChEBI
PulegoneChEBI
IsopulegoneMeSH
Pulegone, (R)-isomerMeSH
Pulegone, (S)-isomerMeSH
cis-IsopulegoneMeSH
(+)-4(8)-Para-menthen-3-oneHMDB
(+)-PulegoneHMDB
(1R)-(+)-P-Menth-4(8)-en-3-oneHMDB
(R)-PulegoneHMDB
D-PulegoneHMDB
FEMA 2963HMDB
P-Menth-4(8)-en-3-oneHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
Traditional Name(+-)-pulegone
CAS Registry NumberNot Available
SMILES
CC1CCC(=C(C)C)C(=O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3
InChI KeyNZGWDASTMWDZIW-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
Mentha aquaticaLOTUS Database
Mentha gattefosseiLOTUS Database
Mentha piperitaLOTUS Database
Mentha pulegiumLOTUS Database
Mentha sachalinensisLOTUS Database
Mentha spicataLOTUS Database
Monarda fistulosaLOTUS Database
Poliomintha incanaLOTUS Database
Pycnanthemum muticumLOTUS Database
Schizonepeta multifidaLOTUS Database
Schizonepeta tenuifoliaLOTUS 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
logP2.36ALOGPS
logP2.86ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.13 m³·mol⁻¹ChemAxon
Polarizability18.34 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 IDFDB014298  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6988  
PDB IDNot Available
ChEBI ID26381  
Good Scents IDNot Available
References
General References
  1. Petretto GL, Fancello F, Zara S, Foddai M, Mangia NP, Sanna ML, Omer EA, Menghini L, Chessa M, Pintore G: Antimicrobial activity against beneficial microorganisms and chemical composition of essential oil of Mentha suaveolens ssp. insularis grown in Sardinia. J Food Sci. 2014 Mar;79(3):M369-77. doi: 10.1111/1750-3841.12343. Epub 2014 Feb  7. [PubMed:24506214  ] 
  2. LOTUS database [Link]