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Showing NP-Card for (R)-Piperitone (NP0048308)

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Record Information
Version2.0
Created at2022-03-17 20:54:24 UTC
Updated at2022-03-17 20:54:24 UTC
NP-MRD IDNP0048308
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-Piperitone
Description(R)-Piperitone, also known as alpha-piperitone, 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, (R)-piperitone is considered to be an isoprenoid lipid molecule (R)-Piperitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-Piperitone is a minty and peppermint tasting compound. Outside of the human body, (R)-Piperitone is found, on average, in the highest concentration within cornmints (R)-Piperitone has also been detected, but not quantified in, herbs and spices and mentha (mint). This could make (R)-piperitone a potential biomarker for the consumption of these foods. (R)-Piperitone is found in Artemisia deserti, Artemisia gmelinii, Artemisia herba-alba, Artemisia judaica, Artemisia koidzumii, Chrysactinia mexicana, Eucalyptus dives, Eucalyptus mitchelliana, Mentha piperita, Piper aduncum and Tyrophagus similis. The (6S)-enantiomer of piperitone.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048308 ((R)-Piperitone)


  Mrv0541 02241214502D          

 11 11  0  0  0  0            999 V2000
   -0.2277   -0.6746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9417   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270    0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869    0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.6757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0048308 ((R)-Piperitone)

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3D SDF for NP0048308 ((R)-Piperitone)

  Mrv0541 02241214502D          

 11 11  0  0  0  0            999 V2000
   -0.2277   -0.6746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9417   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270    0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869    0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.6757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423   -1.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CCC(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1

> <INCHI_KEY>
YSTPAHQEHQSRJD-VIFPVBQESA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.322227807740777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
3.0039530656666673

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.87463872429901

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5581385544298785

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.346799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-piperitone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048308 ((R)-Piperitone)
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PDB for NP0048308 ((R)-Piperitone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.425  -1.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.758  -0.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.758   1.050   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.424   1.820   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.423   3.360   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.909   1.051   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.909  -0.490   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.243  -1.261   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.907  -3.569   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.425  -2.800   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.759  -3.570   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0048308 ((R)-Piperitone)
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SMILES for NP0048308 ((R)-Piperitone)
CC(C)[C@@H]1CCC(C)=CC1=O
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INCHI for NP0048308 ((R)-Piperitone)
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1
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Synonyms
ValueSource
(S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneChEBI
(S)-PiperitoneChEBI
alpha-PiperitoneChEBI
D-PiperitoneChEBI
a-PiperitoneGenerator
Α-piperitoneGenerator
(-)-PiperitoneHMDB
(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneHMDB
(6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-oneHMDB
(6R)-6-Isopropyl-3-methylcyclohex-2-en-1-oneHMDB
L-PiperitoneHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
Traditional Nameα-piperitone
CAS Registry Number4573-50-6
SMILES
CC(C)[C@@H]1CCC(C)=CC1=O
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1
InChI KeyYSTPAHQEHQSRJD-VIFPVBQESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia desertiLOTUS Database
Artemisia gmeliniiLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia koidzumiiLOTUS Database
Chrysactinia mexicanaLOTUS Database
Eucalyptus divesLOTUS Database
Eucalyptus mitchellianaLOTUS Database
MenthaFooDB
Mentha arvensisFooDB
Mentha piperitaLOTUS Database
Mentha spicataFooDB
Piper aduncumLOTUS Database
Tyrophagus similisLOTUS 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
    • 

  • Cyclohexenone
    • 

  • 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
logP2.47ALOGPS
logP3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.35 m³·mol⁻¹ChemAxon
Polarizability18.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035737  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014467  
KNApSAcK IDC00003054  
Chemspider ID96775  
KEGG Compound IDC09885  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107561  
PDB IDNot Available
ChEBI ID41  
Good Scents IDNot Available
References
General References