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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:57:55 UTC
Update Date2021-09-14 15:19:36 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
Data?1563866077
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
Description Belongs to the class of organic compounds known as oxepanes. Oxepanes 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
  • 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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.79331661259
DarkChem[M-H]-158.24231661259
DeepCCS[M-2H]-199.07330932474
DeepCCS[M+Na]+173.73430932474
AllCCS[M+H]+161.832859911
AllCCS[M+H-H2O]+158.132859911
AllCCS[M+NH4]+165.332859911
AllCCS[M+Na]+166.332859911
AllCCS[M-H]-168.932859911
AllCCS[M+Na-2H]-168.932859911
AllCCS[M+HCOO]-169.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DeoxyartemsininC[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C233074.7Standard polar33892256
DeoxyartemsininC[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C231922.3Standard non polar33892256
DeoxyartemsininC[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C232089.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deoxyartemsinin,1TMS,isomer #1C[C@@H]1C=C[C@H]2C3[C@H]1CC[C@@](C)(O[Si](C)(C)C)O[C@@H]3OC(=O)[C@@H]2C2158.8Semi standard non polar33892256
Deoxyartemsinin,1TBDMS,isomer #1C[C@@H]1C=C[C@H]2C3[C@H]1CC[C@@](C)(O[Si](C)(C)C(C)(C)C)O[C@@H]3OC(=O)[C@@H]2C2405.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyartemsinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-5690000000-c472fade044113c825402017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyartemsinin GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9141000000-65583165d952d95370fa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyartemsinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyartemsinin 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 - Deoxyartemsinin 10V, Positive-QTOFsplash10-014i-0190000000-83bd23db6874cc2486a32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Positive-QTOFsplash10-014j-1190000000-396aac6abf9880cf85be2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Positive-QTOFsplash10-0kai-9570000000-3ae434b265a650116f022017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Negative-QTOFsplash10-0aor-0090000000-22ef8eccc2e0800cc1f72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Negative-QTOFsplash10-06di-0090000000-5a12eed7d2b358da3a742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Negative-QTOFsplash10-056r-6920000000-2ed359e26af8536f0b9c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Positive-QTOFsplash10-014i-0090000000-338ee9c9746d3716bbb82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Positive-QTOFsplash10-014i-0190000000-6681a1cebefda6e746a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Positive-QTOFsplash10-05r3-3930000000-a78a8acb6468c93befa02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Negative-QTOFsplash10-014i-0090000000-c6cc318d73093d1123732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Negative-QTOFsplash10-014i-0090000000-9fda6044b1dccf2e8e962021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Negative-QTOFsplash10-06r6-5290000000-4e336d79e9468e52d37d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound156094
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 ReferencesNot Available