Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-07 08:15:17 UTC
Update Date2021-09-26 22:50:27 UTC
HMDB IDHMDB0242731
Secondary Accession NumbersNone
Metabolite Identification
Common NameArteether
Description3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl- belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. Based on a literature review very few articles have been published on 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-. This compound has been identified in human blood as reported by (PMID: 31557052 ). Arteether is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Arteether is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H28O5
Average Molecular Weight312.406
Monoisotopic Molecular Weight312.193674002
IUPAC Name10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecane
Traditional Namearteether
CAS Registry NumberNot Available
SMILES
CCOC1OC2OC3(C)CCC4C(C)CCC(C1C)C24OO3
InChI Identifier
InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3
InChI KeyNLYNIRQVMRLPIQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentArtemisinins
Alternative Parents
Substituents
  • Artemisinin skeleton
  • Oxepane
  • 1,2,4-trioxane
  • Oxane
  • Dialkyl peroxide
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP3.52ALOGPS
logP3.84ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.41 m³·mol⁻¹ChemAxon
Polarizability34.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-207.56330932474
DeepCCS[M+Na]+182.97330932474
AllCCS[M+H]+174.232859911
AllCCS[M+H-H2O]+171.032859911
AllCCS[M+NH4]+177.232859911
AllCCS[M+Na]+178.132859911
AllCCS[M-H]-181.832859911
AllCCS[M+Na-2H]-181.932859911
AllCCS[M+HCOO]-182.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arteether GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5090000000-83616d00d741031362162021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arteether GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arteether 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 - Arteether 10V, Positive-QTOFsplash10-03di-0009000000-b6759757ecbd381b093f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteether 20V, Positive-QTOFsplash10-03di-0059000000-fa041bdcf89b9b102f362021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteether 40V, Positive-QTOFsplash10-054o-7090000000-f38f07229f2d2c795a8e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteether 10V, Negative-QTOFsplash10-03di-0009000000-b96088c3b96fcfb9ab3e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteether 20V, Negative-QTOFsplash10-03di-0019000000-54b7bff5587094b6ce772021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arteether 40V, Negative-QTOFsplash10-0kdi-2090000000-0f2a22d082dd498d7c042021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID437481
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound500080
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]