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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 19:43:36 UTC
Update Date2020-02-26 21:25:08 UTC
HMDB IDHMDB0004487
Secondary Accession Numbers
  • HMDB0061788
  • HMDB04487
  • HMDB61788
Metabolite Identification
Common Name(S)-Carvone
DescriptionCarvone is a volatile terpenoid. Carvone is found in many essential oils and is very abundant in the seeds of caraway (Carum carvi). Carvone is occasionally found as a component of biological fluids in normal individuals. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID: 5556886 , 2477620 , Wikipedia).
Structure
Data?1582752308
Synonyms
ValueSource
(+)-(4S)-CarvoneChEBI
(+)-(S)-CarvoneChEBI
(5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-(+)-CarvoneChEBI
(S)-(+)-p-Mentha-6,8-dien-2-oneChEBI
(S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-oneChEBI
(S)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
CarvolChEBI
CarvoneChEBI
D-(+)-CarvoneChEBI
D-CarvoneChEBI
(+)-CarvoneKegg
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneHMDB
D-p-Mentha-6,8(9)-dien-2-oneHMDB
(S)-CarvoneChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
CAS Registry Number2244-16-8
SMILES
CC(=C)[C@H]1CC=C(C)C(=O)C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1
InChI KeyULDHMXUKGWMISQ-VIFPVBQESA-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1300 mg/L at 18 °CNot Available
LogP1.267Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.77ALOGPS
logP2.55ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.17 m³·mol⁻¹ChemAxon
Polarizability17.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9200000000-b8485ca29dc163ef7386Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9200000000-b8485ca29dc163ef7386Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8l-9200000000-0d07518eb09c4d6d7512Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-cad4b73ca0349a0fca73Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9700000000-4f8b99aefc0ccf7e31f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9600000000-9902205f6d338c08818dSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0a59-9200000000-b8485ca29dc163ef7386Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-62861ac4cbf0b95e5069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-b282dcb5d4a98c3f852fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-0fd631d26260645c64aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-97d37f99bcaf0ed7d108Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-1817a8dceee7a31df4e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6900000000-581a45ee1ec95e201138Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kai-9200000000-87c2472a96aad69404afSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013718
KNApSAcK IDC00010891
Chemspider ID15855
KEGG Compound IDC11383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16724
PDB IDNot Available
ChEBI ID15399
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jager W, Mayer M, Reznicek G, Buchbauer G: Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. J Pharm Pharmacol. 2001 May;53(5):637-42. [PubMed:11370703 ]
  2. Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. [PubMed:8207942 ]
  3. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  4. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]
  5. McHugh D, Hu SS, Rimmerman N, Juknat A, Vogel Z, Walker JM, Bradshaw HB: N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC Neurosci. 2010 Mar 26;11:44. doi: 10.1186/1471-2202-11-44. [PubMed:20346144 ]
  6. Tauber S, Paulsen K, Wolf S, Synwoldt P, Pahl A, Schneider-Stock R, Ullrich O: Regulation of MMP-9 by a WIN-binding site in the monocyte-macrophage system independent from cannabinoid receptors. PLoS One. 2012;7(11):e48272. doi: 10.1371/journal.pone.0048272. Epub 2012 Nov 6. [PubMed:23139770 ]
  7. Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF: N-Arachidonoyl glycine suppresses Na(+)/Ca(2)(+) exchanger-mediated Ca(2)(+) entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. [PubMed:23517055 ]
  8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.