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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:43:45 UTC
Update Date2023-02-21 17:24:52 UTC
HMDB IDHMDB0035714
Secondary Accession Numbers
  • HMDB35714
Metabolite Identification
Common NameEpoxyartemisia ketone
DescriptionEpoxyartemisia ketone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Epoxyartemisia ketone has been detected, but not quantified in, mugworts (Artemisia vulgaris). This could make epoxyartemisia ketone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Epoxyartemisia ketone.
Structure
Data?1677000292
Synonyms
ValueSource
1-(3,3-Dimethyloxiranyl)-2,2-dimethyl-3-buten-1-one, 9ciHMDB
1-(3,3-Dimethyloxiranyl)-2,2-dimethyl-3-buten-1-one-epoxyartemisia ketoneHMDB
5,6-Epoxy-3,3,6-trimethyl-1-hepten-4-oneHMDB
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name1-(3,3-dimethyloxiran-2-yl)-2,2-dimethylbut-3-en-1-one
Traditional Name1-(3,3-dimethyloxiran-2-yl)-2,2-dimethylbut-3-en-1-one
CAS Registry Number79507-83-8
SMILES
CC(C)(C=C)C(=O)C1OC1(C)C
InChI Identifier
InChI=1S/C10H16O2/c1-6-9(2,3)7(11)8-10(4,5)12-8/h6,8H,1H2,2-5H3
InChI KeyVDWHYKNCKVKWIG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility208.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP2.24ALOGPS
logP2.61ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)19.77ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.83 m³·mol⁻¹ChemAxon
Polarizability18.85 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]+138.96631661259
DarkChem[M-H]-135.9331661259
DeepCCS[M+H]+141.96230932474
DeepCCS[M-H]-139.56730932474
DeepCCS[M-2H]-174.90330932474
DeepCCS[M+Na]+149.42430932474
AllCCS[M+H]+136.032859911
AllCCS[M+H-H2O]+132.032859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+140.932859911
AllCCS[M-H]-139.532859911
AllCCS[M+Na-2H]-140.932859911
AllCCS[M+HCOO]-142.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epoxyartemisia ketoneCC(C)(C=C)C(=O)C1OC1(C)C1478.5Standard polar33892256
Epoxyartemisia ketoneCC(C)(C=C)C(=O)C1OC1(C)C1052.1Standard non polar33892256
Epoxyartemisia ketoneCC(C)(C=C)C(=O)C1OC1(C)C1152.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epoxyartemisia ketone,1TMS,isomer #1C=CC(C)(C)C(O[Si](C)(C)C)=C1OC1(C)C1087.7Semi standard non polar33892256
Epoxyartemisia ketone,1TMS,isomer #1C=CC(C)(C)C(O[Si](C)(C)C)=C1OC1(C)C1191.1Standard non polar33892256
Epoxyartemisia ketone,1TBDMS,isomer #1C=CC(C)(C)C(O[Si](C)(C)C(C)(C)C)=C1OC1(C)C1312.1Semi standard non polar33892256
Epoxyartemisia ketone,1TBDMS,isomer #1C=CC(C)(C)C(O[Si](C)(C)C(C)(C)C)=C1OC1(C)C1431.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyartemisia ketone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ke-9000000000-cd26c5dcb1ac3000fe8a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epoxyartemisia ketone 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 - Epoxyartemisia ketone 10V, Positive-QTOFsplash10-014i-5900000000-b40b704062145dbfff9d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Positive-QTOFsplash10-014j-9400000000-f1fb5a3d1db634c12dba2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Positive-QTOFsplash10-014i-9000000000-5f3ea937a4f8ae461b5b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Negative-QTOFsplash10-014i-1900000000-1b5b1f1551fb23d6f9312015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Negative-QTOFsplash10-014i-6900000000-3019ff3543dbee5344772015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Negative-QTOFsplash10-0ab9-9100000000-c8daabdab7b2874e35b42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Positive-QTOFsplash10-014i-8900000000-fd31798f27b86d1cf31b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Positive-QTOFsplash10-066u-9300000000-04d2341bb05c390d0fd82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Positive-QTOFsplash10-0006-9000000000-5babdbceb3647bfdfb162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Negative-QTOFsplash10-014i-0900000000-cb7592114e600c180aec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Negative-QTOFsplash10-014i-4900000000-cdaf73c61af2425584652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Negative-QTOFsplash10-0a4j-9000000000-3fea428da477927280162021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB014437
KNApSAcK IDC00010386
Chemspider ID9990744
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11816089
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1851111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .