Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:57:57 UTC
Update Date2022-09-22 18:34:26 UTC
HMDB IDHMDB0036789
Secondary Accession Numbers
  • HMDB36789
Metabolite Identification
Common NameCaryophyllene alpha-oxide
DescriptionCaryophyllene alpha-oxide, also known as beta-caryophyllene epoxide, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Caryophyllene alpha-oxide.
Structure
Data?1563862927
Synonyms
ValueSource
Caryophyllene a-oxideGenerator
Caryophyllene α-oxideGenerator
(-)-beta-Caryophyllene epoxideHMDB
(-)-EpoxydihydrocaryophylleneHMDB
beta-Caryophyllene epoxideHMDB
beta-Caryophyllene oxideHMDB
Caryophylene oxideHMDB
Caryophyllene epoxideHMDB
Caryophyllene oxydeHMDB
Caryophyllene oxideHMDB
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane
Traditional Namecaryophyllene oxide
CAS Registry Number1139-30-6
SMILES
CC12CCC3C(CC3(C)C)C(=C)CCC1O2
InChI Identifier
InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3
InChI KeyNVEQFIOZRFFVFW-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
  • Caryophyllane sesquiterpenoid
  • Sesquiterpenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point63.5 - 64 °CNot Available
Boiling Point279.68 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.21 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.429 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP3.49ALOGPS
logP3.62ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.21 m³·mol⁻¹ChemAxon
Polarizability26.42 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]+153.80531661259
DarkChem[M-H]-149.98631661259
DeepCCS[M-2H]-188.58430932474
DeepCCS[M+Na]+163.81130932474
AllCCS[M+H]+152.832859911
AllCCS[M+H-H2O]+149.032859911
AllCCS[M+NH4]+156.432859911
AllCCS[M+Na]+157.432859911
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
Caryophyllene alpha-oxideCC12CCC3C(CC3(C)C)C(=C)CCC1O22035.5Standard polar33892256
Caryophyllene alpha-oxideCC12CCC3C(CC3(C)C)C(=C)CCC1O21550.9Standard non polar33892256
Caryophyllene alpha-oxideCC12CCC3C(CC3(C)C)C(=C)CCC1O21584.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Caryophyllene alpha-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2920000000-d2a03a5c7a66db83ceba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caryophyllene alpha-oxide 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 - Caryophyllene alpha-oxide 10V, Positive-QTOFsplash10-00di-0090000000-f8f0be1391f197a799e12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOFsplash10-0fk9-2490000000-fa2d7bb36e26ed2644872015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOFsplash10-0pb9-9400000000-abbf14c22de1acb12c5a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOFsplash10-00di-0090000000-f8f0be1391f197a799e12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOFsplash10-0fk9-2490000000-fa2d7bb36e26ed2644872015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOFsplash10-0pb9-9400000000-abbf14c22de1acb12c5a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOFsplash10-00di-0090000000-f8f0be1391f197a799e12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOFsplash10-0fk9-2490000000-fa2d7bb36e26ed2644872015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOFsplash10-0pb9-9400000000-abbf14c22de1acb12c5a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOFsplash10-014i-0090000000-0c846f045345079a830d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOFsplash10-014i-1190000000-c8390951524f03b712692015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOFsplash10-0pdi-8930000000-6906b65254e00eb839852015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOFsplash10-014i-0090000000-0c846f045345079a830d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOFsplash10-014i-1190000000-c8390951524f03b712692015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOFsplash10-0pdi-8930000000-6906b65254e00eb839852015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOFsplash10-014i-0090000000-0c846f045345079a830d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOFsplash10-014i-1190000000-c8390951524f03b712692015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOFsplash10-0pdi-8930000000-6906b65254e00eb839852015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOFsplash10-0fk9-0190000000-86d27f80d48351d7768e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOFsplash10-0a4i-9760000000-2b1f639fb3d3df83de232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOFsplash10-06r7-9500000000-f6be54a6f8d006ed95482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOFsplash10-014i-0090000000-d46df74fb0403a6b84f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOFsplash10-014i-0090000000-554eee2e2df3c86c88102021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015733
KNApSAcK IDC00012483
Chemspider ID13711
KEGG Compound IDC16908
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14350
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1023631
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.