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Record Information
Version3.6
Creation Date2013-06-15 16:57:55 UTC
Update Date2016-02-11 08:08:28 UTC
HMDB IDHMDB60569
Secondary Accession NumbersNone
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=1/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+/s2
InChI KeyInChIKey=ZHHCFKHSMKRNCX-UXQJZWOSNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.99 m3·mol-1ChemAxon
Polarizability28.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60569
Metagene LinkHMDB60569
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