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Record Information
Version4.0
Creation Date2013-06-15 16:57:55 UTC
Update Date2017-09-27 08:43:50 UTC
HMDB IDHMDB0060569
Secondary Accession Numbers
  • HMDB60569
Metabolite Identification
Common NameDeoxyartemsinin
DescriptionDeoxyartemsinin is a metabolite of artemisinin. Artemisinin, also known as Qinghaosu, and its derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. The starting compound artemisinin is isolated from the plant Artemisia annua, sweet wormwood, an herb employed in Chinese traditional medicine. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H22O4
Average Molecular Weight266.3328
Monoisotopic Molecular Weight266.151809192
IUPAC Name(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one
Traditional Name(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23
InChI Identifier
InChI=1S/C15H22O4/c1-8-4-5-11-9(2)13(16)18-14-12(11)10(8)6-7-15(3,17)19-14/h4-5,8-12,14,17H,6-7H2,1-3H3/t8-,9-,10+,11-,12?,14+,15+/m1/s1
InChI KeyZHHCFKHSMKRNCX-CRBWWJEESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oxepanes. These are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxepanes
Direct ParentOxepanes
Alternative Parents
Substituents
  • Delta valerolactone
  • Delta_valerolactone
  • Oxepane
  • Oxane
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.14 g/LALOGPS
logP1.27ALOGPS
logP2.22ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.26ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.99 m³·mol⁻¹ChemAxon
Polarizability28.86 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-5690000000-c472fade044113c82540View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9141000000-65583165d952d95370faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-83bd23db6874cc2486a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1190000000-396aac6abf9880cf85beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9570000000-3ae434b265a650116f02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0090000000-22ef8eccc2e0800cc1f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06di-0090000000-5a12eed7d2b358da3a74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6920000000-2ed359e26af8536f0b9cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00826
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available