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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:54:30 UTC
Update Date2023-02-21 17:24:30 UTC
HMDB IDHMDB0034974
Secondary Accession Numbers
  • HMDB34974
Metabolite Identification
Common Name(R)-Carvotanacetone
Description(R)-Carvotanacetone 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. Based on a literature review a significant number of articles have been published on (R)-Carvotanacetone.
Structure
Data?1677000270
Synonyms
ValueSource
(-)-CarvotanacetoneHMDB
AndrocurHMDB
CyprostatHMDB
Cyprosterone acetateHMDB
Cyproteron acetateHMDB
Cyproteron-R acetateHMDB
Cyproterone 17-O-acetateHMDB
Cyproterone 17alpha-acetateHMDB
Cyproterone acetateHMDB
CyproteroneacetateHMDB
Carvone, (S)-isomerMeSH
Limonen-6-oneMeSH
CarvoneMeSH
(RS)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneMeSH
2-Methyl-5-isopropenyl-2-cyclohexenoneMeSH
5-Isopropyl-2-methyl-2-cyclohexen-1-oneMeSH
Carvone, (R)-isomerMeSH
2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-oneMeSH
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2-methyl-5-(propan-2-yl)cyclohex-2-en-1-one
Traditional Name5-isopropyl-2-methylcyclohex-2-en-1-one
CAS Registry Number33375-08-5
SMILES
CC(C)C1CC=C(C)C(=O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,7,9H,5-6H2,1-3H3
InChI KeyWPGPCDVQHXOMQP-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.75ALOGPS
logP2.9ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.4 m³·mol⁻¹ChemAxon
Polarizability18.4 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]+134.68431661259
DarkChem[M-H]-132.08131661259
DeepCCS[M+H]+140.00330932474
DeepCCS[M-H]-136.25730932474
DeepCCS[M-2H]-173.71230932474
DeepCCS[M+Na]+149.14930932474
AllCCS[M+H]+132.232859911
AllCCS[M+H-H2O]+127.732859911
AllCCS[M+NH4]+136.332859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-139.532859911
AllCCS[M+HCOO]-141.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-CarvotanacetoneCC(C)C1CC=C(C)C(=O)C11662.2Standard polar33892256
(R)-CarvotanacetoneCC(C)C1CC=C(C)C(=O)C11243.1Standard non polar33892256
(R)-CarvotanacetoneCC(C)C1CC=C(C)C(=O)C11247.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Carvotanacetone,1TMS,isomer #1CC1=CCC(C(C)C)C=C1O[Si](C)(C)C1375.5Semi standard non polar33892256
(R)-Carvotanacetone,1TMS,isomer #1CC1=CCC(C(C)C)C=C1O[Si](C)(C)C1288.2Standard non polar33892256
(R)-Carvotanacetone,1TBDMS,isomer #1CC1=CCC(C(C)C)C=C1O[Si](C)(C)C(C)(C)C1606.6Semi standard non polar33892256
(R)-Carvotanacetone,1TBDMS,isomer #1CC1=CCC(C(C)C)C=C1O[Si](C)(C)C(C)(C)C1485.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Carvotanacetone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9300000000-2f8475f123b9e8cdea642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Carvotanacetone 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 - (R)-Carvotanacetone 10V, Positive-QTOFsplash10-0udi-0900000000-cb7d76cf6095237c0f172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Positive-QTOFsplash10-0udi-9800000000-60c503e1ff2723928a462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Positive-QTOFsplash10-100r-9000000000-375dcdd5898f683b6be02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Negative-QTOFsplash10-0udi-0900000000-f82c83439c41b14152112016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Negative-QTOFsplash10-0udi-0900000000-ad15e054514d8515c9952016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Negative-QTOFsplash10-0f7c-9800000000-ec4477331d3c1cefd4482016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Positive-QTOFsplash10-0w29-3900000000-3979614d67936e2eab402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Positive-QTOFsplash10-055f-9200000000-8dd2756f6e2ca7142cf02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Positive-QTOFsplash10-0006-9000000000-0a06a9c60be1f46855b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Negative-QTOFsplash10-0udi-0900000000-6bf96790df77f609bfa82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Negative-QTOFsplash10-0gbm-9700000000-806e27bdb4cfeeb5926e2021-09-22Wishart 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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014523
KNApSAcK IDC00052126
Chemspider ID454694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521267
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.