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Showing NP-Card for piperitone oxide (NP0044992)

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Record Information
Version2.0
Created at2022-03-10 18:52:24 UTC
Updated at2022-03-10 22:22:12 UTC
NP-MRD IDNP0044992
Secondary Accession NumbersNone
Natural Product Identification
Common Namepiperitone oxide
DescriptionPiperitone oxide is an oxidized derivative of Piperitone. It belongs to the class of organic compounds known cyclic monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Piperitone oxide exists as two isomers, cis-Piperitone oxide and trans-Piperitone oxide. It is a colorless to pale yellow clear liquid that is neutral, hydrophobic and essentially insoluble in water. Piperitone oxide can be found in cornmint, orange mint, peppermint, and spearmint, which makes piperitone oxide a potential biomarker for the consumption of these food products. It has also been detected in the essential oils of other mint species, such as apple mint (Mentha suaveolens) (PMID: 25985361 ). Piperitone oxide has also been detected in Cannabis sativa plants (PMID: 6991645 ). It is one of more than 140 terpenoids found in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044992 (piperitone oxide)


  Mrv1652303192001293D          

 12 13  0  0  0  0            999 V2000
   -2.5893    1.4739    0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -0.7668   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -0.3983    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694    1.0038    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398    0.9261   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9675    0.0958    0.3248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6304    0.1042   -0.3625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0269   -1.2529   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -1.4926    0.0150 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3007   -0.4142   -0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7169   -2.1977   -0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -1.4043   -1.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  6  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0044992 (piperitone oxide)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.7320   -1.0827    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267    0.2310   -0.2078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7366    1.3055    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083    0.0881    0.2767 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1041   -1.0420   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -1.2035    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172    0.0047    0.0659 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5842   -0.1836   -0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    0.8521    1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695    1.2859    0.0294 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2014    1.3124    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.3708   -0.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7983   -0.9007    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -1.5226    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -1.7623   -0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539    0.3969   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    1.7661    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732    2.1274   -0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6828    0.9547    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6622   -0.1993    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189   -2.0076   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215   -0.7782   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793   -1.3972    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713   -2.1243   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8186    0.7344   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355   -0.3116   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -1.0382   -1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    2.1236   -0.4881 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  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  4  1  0
 10  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  6
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  6
M  END
Download

3D SDF for NP0044992 (piperitone oxide)


  Mrv1652303192001293D          

 12 13  0  0  0  0            999 V2000
   -2.5893    1.4739    0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -0.7668   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814   -0.3983    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694    1.0038    0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398    0.9261   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9675    0.0958    0.3248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6304    0.1042   -0.3625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0269   -1.2529   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -1.4926    0.0150 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3007   -0.4142   -0.2123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7169   -2.1977   -0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -1.4043   -1.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  6  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1

> <INCHI_KEY>
IAFONZHDZMCORS-QNSHHTMESA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.236

> <EXACT_MASS>
168.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.96877720325932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,6S)-6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
2.2590790173333337

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.696022255772977

> <JCHEM_PKA_STRONGEST_BASIC>
-4.280332456179142

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
45.953300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0044992 (piperitone oxide)

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PDB for NP0044992 (piperitone oxide)
HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.589   1.474   0.392  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.900  -0.767  -0.500  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.581  -0.398   0.594  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.369   1.004   0.348  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.640   0.926  -0.477  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.968   0.096   0.325  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.630   0.104  -0.363  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.027  -1.253  -0.361  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.375  -1.493   0.015  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.301  -0.414  -0.212  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.717  -2.198  -0.681  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.236  -1.404  -1.163  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3   10                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    1    2    7                                                  
CONECT    7    4    6    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   12                                                  
CONECT   10    3    5    9   12                                             
CONECT   11    8                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0044992 (piperitone oxide)
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SMILES for NP0044992 (piperitone oxide)
CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O
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INCHI for NP0044992 (piperitone oxide)
InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O2
Average Mass168.2360 Da
Monoisotopic Mass168.11503 Da
IUPAC Name(1S,3R,6S)-6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one
Traditional Name(1S,3R,6S)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
CAS Registry Number4713-38-6
SMILES
CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O
InChI Identifier
InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1
InChI KeyIAFONZHDZMCORS-QNSHHTMESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calamintha nepeta subsp. glandulosaPlant
Calamintha nepeta subsp.glandulosa.Plant
Cannabis sativaNULL
      Not Available
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha piperita L.Plant
Mentha rotundifoliaPlant
Mentha sauveolensPlant
Mentha spicataFooDB
Mentha sylvestrisPlant
Mentha x piperitaFooDB
Veronica spicataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxepanes  
Sub ClassNot Available
Direct ParentOxepanes  
Alternative Parents
Substituents
  • Oxepane
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP1.96ALOGPS
logP2.26ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)19.7ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.95 m³·mol⁻¹ChemAxon
Polarizability18.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6430800  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References