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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:57:59 UTC
Update Date2017-12-07 17:17:55 UTC
HMDB IDHMDB0060570
Secondary Accession Numbers
  • HMDB60570
Metabolite Identification
Common NameDeoxydihydro-artemisinin
DescriptionDeoxydihydro-artemisinin 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 FormulaC15H24O4
Average Molecular Weight268.3487
Monoisotopic Molecular Weight268.167459256
IUPAC Name(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol
Traditional Name(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4
InChI Identifier
InChI=1S/C15H24O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12?,13-,14?,15-/m1/s1
InChI KeyJQGOBHOUYKYFPD-YONALABKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dioxolopyrans. These are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDioxolopyrans
Direct ParentDioxolopyrans
Alternative Parents
Substituents
  • Dioxolopyran
  • Ketal
  • Oxepane
  • Oxane
  • Meta-dioxolane
  • Hemiacetal
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility2.23 g/LALOGPS
logP2.09ALOGPS
logP2.65ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.12ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.83 m³·mol⁻¹ChemAxon
Polarizability29.42 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0zi0-6290000000-bd14a8d092a3bee64c65View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9223000000-7d969d6919602d3f4e3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-e455e0a72274f43bb7fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1090000000-5ef1625041d20f32efdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9110000000-31dcde3255d244134837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0090000000-c3d5d3f5efc5c3db114fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0290000000-dd4313ddfc322d5bd263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xu-1900000000-1e26c3fb2ac2255ba21cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDDBMET00827
      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