Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:54:37 UTC
Update Date2022-03-07 02:54:40 UTC
HMDB IDHMDB0035869
Secondary Accession Numbers
  • HMDB35869
Metabolite Identification
Common Namealpha-Rotunol
Descriptionalpha-Rotunol, also known as a-rotunol, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on alpha-Rotunol.
Structure
Data?1563862785
Synonyms
ValueSource
a-RotunolGenerator
Α-rotunolGenerator
[4AS-(4aalpha,6beta,8abeta)]-4a,5,6,7,8,8a-hexahydro-4a-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)-2(1H)-naphthalenoneHMDB
b-RotunolGenerator
Β-rotunolGenerator
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one
Traditional Name4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-5,6,7,8-tetrahydro-1H-naphthalen-2-one
CAS Registry Number24405-56-9
SMILES
CC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C1
InChI Identifier
InChI=1S/C15H22O2/c1-10(2)12-5-6-14(4)9-13(16)7-11(3)15(14,17)8-12/h7,12,17H,1,5-6,8-9H2,2-4H3
InChI KeyWDFLKCAWQQMJCA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
Alternative Parents
Substituents
  • Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87.5 - 88.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility121.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.46ALOGPS
logP2.7ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.77ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.44 m³·mol⁻¹ChemAxon
Polarizability26.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.96431661259
DarkChem[M-H]-151.56631661259
DeepCCS[M+H]+161.3630932474
DeepCCS[M-H]-159.00230932474
DeepCCS[M-2H]-192.10430932474
DeepCCS[M+Na]+167.45330932474
AllCCS[M+H]+155.432859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+158.932859911
AllCCS[M+Na]+159.932859911
AllCCS[M-H]-162.132859911
AllCCS[M+Na-2H]-162.532859911
AllCCS[M+HCOO]-163.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-RotunolCC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C13010.7Standard polar33892256
alpha-RotunolCC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C11796.4Standard non polar33892256
alpha-RotunolCC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C11933.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Rotunol,1TMS,isomer #1C=C(C)C1CCC2(C)CC(=O)C=C(C)C2(O[Si](C)(C)C)C12028.3Semi standard non polar33892256
alpha-Rotunol,1TMS,isomer #2C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O)C11987.2Semi standard non polar33892256
alpha-Rotunol,2TMS,isomer #1C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O[Si](C)(C)C)C11950.4Semi standard non polar33892256
alpha-Rotunol,2TMS,isomer #1C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O[Si](C)(C)C)C11958.8Standard non polar33892256
alpha-Rotunol,1TBDMS,isomer #1C=C(C)C1CCC2(C)CC(=O)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C12273.4Semi standard non polar33892256
alpha-Rotunol,1TBDMS,isomer #2C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O)C12217.9Semi standard non polar33892256
alpha-Rotunol,2TBDMS,isomer #1C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C12406.1Semi standard non polar33892256
alpha-Rotunol,2TBDMS,isomer #1C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C12415.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Rotunol GC-MS (Non-derivatized) - 70eV, Positivesplash10-015d-9520000000-7f204ce9c3a9ca728c822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Rotunol GC-MS (1 TMS) - 70eV, Positivesplash10-006x-6090000000-51946f21782ce8c1dfd32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Rotunol 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 - alpha-Rotunol 10V, Negative-QTOFsplash10-001i-0090000000-462acfe4e44a2d558f812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Negative-QTOFsplash10-001i-0090000000-196f7d26364442dc650d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Negative-QTOFsplash10-0gb9-3960000000-c98bf03080f51e9baf452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Negative-QTOFsplash10-001i-0090000000-096295cb81e359e186672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Negative-QTOFsplash10-0fs9-2910000000-a1829c2a73845cf311ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Positive-QTOFsplash10-014r-0290000000-fdf8209b97f5396811e12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Positive-QTOFsplash10-014i-5690000000-af1926a67454fbc887ab2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Positive-QTOFsplash10-0uxv-9310000000-294cb7d800d088fb26052016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Positive-QTOFsplash10-004i-0920000000-3fa5e82ae57b9c864daf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Positive-QTOFsplash10-0gdi-3920000000-4f68e880120bd4526cde2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Positive-QTOFsplash10-05ql-9800000000-c616a56b3168e3bc97a82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB014650
KNApSAcK IDC00012842
Chemspider ID35014038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12315078
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1852201
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.