R-(-)-Carvone (CHEM017689)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:32:46 UTC
Update Date2016-11-09 01:15:39 UTC
Accession NumberCHEM017689
Identification
Common NameR-(-)-Carvone
ClassSmall Molecule
DescriptionA carvone having (S) configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass150.218 g/mol
Monoisotopic Mass150.104 g/mol
CAS Registry Number6485-40-1
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
SMILESCC(=C)[C@@H]1CC=C(C)C(=O)C1
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
InChI KeyULDHMXUKGWMISQ-SECBINFHSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9300000000-4251d272babda4de5c36Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-424a2cd188d1d2f5213dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-8101d73f0cfb2435bca7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0aou-9200000000-f171ea0515bba0d8369dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udj-9500000000-9859933bdc05bac9d663Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9100000000-935629946779efc8b4ffSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-f279f95a33eb225c1b14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07eg-9400000000-34f0a30acb50659192b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-7b658cbdc17dd03f44edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c0270d719fd67ba328d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-9700000000-dfa5cb40b47870793316Spectrum
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004487
FooDB IDFDB013718
Phenol Explorer IDNot Available
KNApSAcK IDC00010891
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID15855
ChEBI ID15399
PubChem Compound ID16724
Kegg Compound IDC11383
YMDB IDYMDB15980
ECMDB IDM2MDB005645
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11380545
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7. 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.
8. 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.
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10. 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.
11. 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.
12. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
13. The lipid handbook with CD-ROM