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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:35:00 UTC
Update Date2021-10-13 06:56:43 UTC
HMDB IDHMDB0036443
Secondary Accession Numbers
  • HMDB36443
Metabolite Identification
Common NameRotundone
DescriptionRotundone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Rotundone.
Structure
Data?1563862876
SynonymsNot Available
Chemical FormulaC15H22O
Average Molecular Weight218.34
Monoisotopic Molecular Weight218.167065328
IUPAC Name3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulen-1-one
Traditional Name3,8-dimethyl-5-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
CAS Registry Number18374-76-0
SMILES
CC1CC(=O)C2=C1CC(CCC2C)C(C)=C
InChI Identifier
InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3
InChI KeyNUWMTBMCSQWPDG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.98 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP10(4.04) g/LALOGPS
logP10(3.8) g/LChemAxon
logS10(-3.3) g/LALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.95 m³·mol⁻¹ChemAxon
Polarizability26.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.63431661259
DarkChem[M-H]-148.21431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rotundone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-7930000000-f41b58dbffe47cd961d32017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rotundone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rotundone 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 - Rotundone 10V, Positive-QTOFsplash10-014i-0290000000-b4f3ffccd9908e72609d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 20V, Positive-QTOFsplash10-016r-1950000000-102fce150de6a306ef492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 40V, Positive-QTOFsplash10-1001-9610000000-ec36640abe14173fc7be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 10V, Negative-QTOFsplash10-014i-0090000000-6271c68eed652c012a8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 20V, Negative-QTOFsplash10-014i-0190000000-b9a0009456e23bcff0962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 40V, Negative-QTOFsplash10-0f76-6920000000-fb0971a924abbb7db9892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 10V, Positive-QTOFsplash10-014i-0390000000-626b704bc7a58edaf5d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 20V, Positive-QTOFsplash10-05rs-2910000000-c915a64affda843736902021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 40V, Positive-QTOFsplash10-0a4i-5900000000-591237cb80f0c863d5b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 20V, Negative-QTOFsplash10-014i-0190000000-ab85dae8587f91154ad42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundone 40V, Negative-QTOFsplash10-006t-0910000000-89931e0a94b89a4b87a02021-09-25Wishart 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 IDFDB015330
KNApSAcK IDC00020397
Chemspider ID35014148
KEGG Compound IDC17501
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRotundone
METLIN IDNot Available
PubChem Compound12315073
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1081281
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.