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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:54:33 UTC
Update Date2023-02-21 17:24:31 UTC
HMDB IDHMDB0034975
Secondary Accession Numbers
  • HMDB34975
Metabolite Identification
Common NamePiperitone
DescriptionPiperitone is found in ceylan cinnamon. Piperitone is a flavouring ingredient.Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (Wikipedia
Structure
Data?1677000271
Synonyms
ValueSource
3-CarvomenthenoneChEBI
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneChEBI
6-Isopropyl-3-methylcyclohex-2-enoneChEBI
p-Menth-1-en-3-oneChEBI
(+-)-PiperitoneHMDB
1-Methyl-4-isopropyl-1-cyclohexen-3-oneHMDB
3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-oneHMDB
6-Isopropyl-3-methyl-2-cyclohexen-1-oneHMDB
DL-PiperitoneHMDB
FEMA 2910HMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
Traditional Namepiperitone
CAS Registry Number89-81-6
SMILES
CC(C)C1CCC(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
InChI KeyYSTPAHQEHQSRJD-UHFFFAOYSA-N
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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point233.00 to 235.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP2.85Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.21631661259
DarkChem[M-H]-134.23931661259
DeepCCS[M+H]+136.38730932474
DeepCCS[M-H]-132.89330932474
DeepCCS[M-2H]-170.130932474
DeepCCS[M+Na]+145.26630932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.632859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.432859911
AllCCS[M-H]-137.632859911
AllCCS[M+Na-2H]-139.232859911
AllCCS[M+HCOO]-141.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiperitoneCC(C)C1CCC(C)=CC1=O1709.4Standard polar33892256
PiperitoneCC(C)C1CCC(C)=CC1=O1203.2Standard non polar33892256
PiperitoneCC(C)C1CCC(C)=CC1=O1231.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piperitone,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC11391.6Semi standard non polar33892256
Piperitone,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC11333.6Standard non polar33892256
Piperitone,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC11626.1Semi standard non polar33892256
Piperitone,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC11540.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Piperitone EI-B (Non-derivatized)splash10-01qi-9300000000-f92830f958dd7b7816c02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Piperitone EI-B (Non-derivatized)splash10-01qi-9300000000-f92830f958dd7b7816c02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperitone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9300000000-e3bec6231e4993e3d5782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperitone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 10V, Positive-QTOFsplash10-0udi-0900000000-0f2176d975b2f9bfe7fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 20V, Positive-QTOFsplash10-0w29-7900000000-bc07a247759df113c9432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 40V, Positive-QTOFsplash10-0a4l-9000000000-6e8d2587c3fab7a87b032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 10V, Negative-QTOFsplash10-0udi-0900000000-83fb585962f6ed48b3782016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 20V, Negative-QTOFsplash10-0udi-0900000000-a2b215f78ea2edceb56c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 40V, Negative-QTOFsplash10-0a4u-8900000000-058070ac2054c97f9a302016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 10V, Positive-QTOFsplash10-0w29-1900000000-cf5ff8ec6a34a5b6435b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 20V, Positive-QTOFsplash10-0gb9-9200000000-ddaec970d54edc7cbf792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 40V, Positive-QTOFsplash10-00kf-9000000000-4c75828fad35f0eec3742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 20V, Negative-QTOFsplash10-0udi-0900000000-3f9a24ef7ca3da32a5222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitone 40V, Negative-QTOFsplash10-014i-9400000000-172af5b361384699caf72021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013573
KNApSAcK IDC00003054
Chemspider ID6721
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperitone
METLIN IDNot Available
PubChem Compound6987
PDB IDNot Available
ChEBI ID48933
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1049441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.