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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:39:20 UTC
Update Date2022-03-07 02:54:35 UTC
HMDB IDHMDB0035645
Secondary Accession Numbers
  • HMDB35645
Metabolite Identification
Common NameEpoxyguaiene
DescriptionEpoxyguaiene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Epoxyguaiene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862750
Synonyms
ValueSource
1a,5a-Epoxy-11-guaieneHMDB
1alpha,5alpha-Epoxy-alpha-guaieneHMDB
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0¹,⁷]undecane
Traditional Name2,8-dimethyl-5-(prop-1-en-2-yl)-11-oxatricyclo[5.3.1.0¹,⁷]undecane
CAS Registry Number10410-05-6
SMILES
CC1CCC23OC12CC(CCC3C)C(C)=C
InChI Identifier
InChI=1S/C15H24O/c1-10(2)13-6-5-11(3)14-8-7-12(4)15(14,9-13)16-14/h11-13H,1,5-9H2,2-4H3
InChI KeyRGRYQUWGSJPMMK-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.0065 g/LALOGPS
logP4.29ALOGPS
logP3.91ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.07 m³·mol⁻¹ChemAxon
Polarizability27.07 ųChemAxon
Number of Rings3ChemAxon
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]+152.20431661259
DarkChem[M-H]-146.40331661259
DeepCCS[M-2H]-187.7430932474
DeepCCS[M+Na]+163.30330932474
AllCCS[M+H]+151.832859911
AllCCS[M+H-H2O]+148.032859911
AllCCS[M+NH4]+155.432859911
AllCCS[M+Na]+156.432859911
AllCCS[M-H]-160.832859911
AllCCS[M+Na-2H]-161.032859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EpoxyguaieneCC1CCC23OC12CC(CCC3C)C(C)=C1881.5Standard polar33892256
EpoxyguaieneCC1CCC23OC12CC(CCC3C)C(C)=C1570.3Standard non polar33892256
EpoxyguaieneCC1CCC23OC12CC(CCC3C)C(C)=C1552.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyguaiene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7l-9810000000-80543d8b709cccf9a0da2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyguaiene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyguaiene 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 - Epoxyguaiene 10V, Positive-QTOFsplash10-00di-0190000000-d80571c5b4244fe1a3c82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 20V, Positive-QTOFsplash10-00di-2690000000-7994e2218d4650739d042016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 40V, Positive-QTOFsplash10-0a4i-9000000000-78314d84883a5ca071412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 10V, Negative-QTOFsplash10-014i-0090000000-0747f8dc24c48b710ebd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 20V, Negative-QTOFsplash10-014i-0090000000-02013427d0951829b2fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 40V, Negative-QTOFsplash10-052g-9410000000-2690f9fdf1e7a10cd17d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 20V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 40V, Negative-QTOFsplash10-02t9-0590000000-bf3cfabffb041351d3272021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 10V, Positive-QTOFsplash10-00di-0290000000-0b37cc2e530c0ef54b492021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 20V, Positive-QTOFsplash10-05fr-9540000000-c02f3eb2acab91cbf18a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyguaiene 40V, Positive-QTOFsplash10-01b9-9240000000-596654d894038e20f4a32021-09-25Wishart 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 IDFDB014355
KNApSAcK IDC00020378
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78384887
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.