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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:22:13 UTC
Update Date2022-03-07 02:54:29 UTC
HMDB IDHMDB0035391
Secondary Accession Numbers
  • HMDB35391
Metabolite Identification
Common NamePreisocalamendiol
DescriptionPreisocalamendiol belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Based on a literature review a small amount of articles have been published on Preisocalamendiol.
Structure
Data?1563862712
Synonyms
ValueSource
NeocurdioneHMDB
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name(5Z)-5-methyl-9-methylidene-2-(propan-2-yl)cyclodec-5-en-1-one
Traditional Name(5Z)-2-isopropyl-5-methyl-9-methylidenecyclodec-5-en-1-one
CAS Registry Number25645-19-6
SMILES
CC(C)C1CC\C(C)=C/CCC(=C)CC1=O
InChI Identifier
InChI=1S/C15H24O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h6,11,14H,4-5,7-10H2,1-3H3/b12-6-
InChI KeyQTFJNWQFKJITEE-SDQBBNPISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGermacrane sesquiterpenoids
Alternative Parents
Substituents
  • Germacrane sesquiterpenoid
  • 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 Point315.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.34 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.940 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.38ALOGPS
logP4.36ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)16.6ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.1 m³·mol⁻¹ChemAxon
Polarizability26.73 ųChemAxon
Number of Rings1ChemAxon
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]+154.28331661259
DarkChem[M-H]-153.52831661259
DeepCCS[M+H]+154.77730932474
DeepCCS[M-H]-151.43730932474
DeepCCS[M-2H]-188.03230932474
DeepCCS[M+Na]+163.57130932474
AllCCS[M+H]+152.232859911
AllCCS[M+H-H2O]+148.232859911
AllCCS[M+NH4]+155.932859911
AllCCS[M+Na]+156.932859911
AllCCS[M-H]-159.132859911
AllCCS[M+Na-2H]-159.832859911
AllCCS[M+HCOO]-160.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PreisocalamendiolCC(C)C1CC\C(C)=C/CCC(=C)CC1=O1996.4Standard polar33892256
PreisocalamendiolCC(C)C1CC\C(C)=C/CCC(=C)CC1=O1578.3Standard non polar33892256
PreisocalamendiolCC(C)C1CC\C(C)=C/CCC(=C)CC1=O1594.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Preisocalamendiol,1TMS,isomer #1C=C1CC/C=C(/C)CCC(C(C)C)=C(O[Si](C)(C)C)C11773.0Semi standard non polar33892256
Preisocalamendiol,1TMS,isomer #1C=C1CC/C=C(/C)CCC(C(C)C)=C(O[Si](C)(C)C)C11748.6Standard non polar33892256
Preisocalamendiol,1TMS,isomer #2C=C1C=C(O[Si](C)(C)C)C(C(C)C)CC/C(C)=C\CC11807.5Semi standard non polar33892256
Preisocalamendiol,1TMS,isomer #2C=C1C=C(O[Si](C)(C)C)C(C(C)C)CC/C(C)=C\CC11766.3Standard non polar33892256
Preisocalamendiol,1TBDMS,isomer #1C=C1CC/C=C(/C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C11998.8Semi standard non polar33892256
Preisocalamendiol,1TBDMS,isomer #1C=C1CC/C=C(/C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C11908.5Standard non polar33892256
Preisocalamendiol,1TBDMS,isomer #2C=C1C=C(O[Si](C)(C)C(C)(C)C)C(C(C)C)CC/C(C)=C\CC12002.6Semi standard non polar33892256
Preisocalamendiol,1TBDMS,isomer #2C=C1C=C(O[Si](C)(C)C(C)(C)C)C(C(C)C)CC/C(C)=C\CC11885.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Preisocalamendiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9580000000-9b09b882c2de4856a79b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Preisocalamendiol 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 - Preisocalamendiol 10V, Positive-QTOFsplash10-00di-0290000000-ed722e6ca4bb4327cab22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 20V, Positive-QTOFsplash10-00b9-2950000000-89246d94d781335954af2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 40V, Positive-QTOFsplash10-0le9-9610000000-488951d4a04aa29bd8a52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 10V, Negative-QTOFsplash10-014i-0090000000-3c3096f5144f3832cff92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 20V, Negative-QTOFsplash10-014i-0390000000-59aa3600813d607b4e612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 40V, Negative-QTOFsplash10-0006-9810000000-8c56b40566a17a51f7072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 20V, Negative-QTOFsplash10-0gb9-0090000000-9d3e6ec8b0fb16bcbfd02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 40V, Negative-QTOFsplash10-004i-0920000000-a468310a585b3a6700682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 10V, Positive-QTOFsplash10-0udi-0090000000-c6a53b706b3a89e8ae4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 20V, Positive-QTOFsplash10-0udi-0290000000-df87aa531b414c699e5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Preisocalamendiol 40V, Positive-QTOFsplash10-0bvl-1910000000-5fef6e970ce9337c189f2021-09-23Wishart 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 IDFDB014066
KNApSAcK IDC00011714
Chemspider ID35013920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12305704
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1619601
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.