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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:24:02 UTC
Update Date2021-09-14 15:19:35 UTC
HMDB IDHMDB0060593
Secondary Accession Numbers
  • HMDB60593
Metabolite Identification
Common NameAlpha-dihydroartemisinin
DescriptionAlpha-dihydroartemisinin 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?1563866079
Synonyms
ValueSource
a-DihydroartemisininGenerator
Α-dihydroartemisininGenerator
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomerHMDB
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomerHMDB
DihydroartemisinineHMDB
DihydroqinghaosuHMDB
DihydroquinghaosuHMDB
DihydroartemisininHMDB
3alpha-HydroxydeoxydihydroartemisininMeSH
9alpha-HydroxydeoxyartemisininMeSH
8alpha-HydroxydeoxyartemisininMeSH
Chemical FormulaC15H24O5
Average Molecular Weight284.3481
Monoisotopic Molecular Weight284.162373878
IUPAC Name(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol
Traditional Nameartenimol
CAS Registry Number81496-81-3
SMILES
C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4
InChI Identifier
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14?,15-/m1/s1
InChI KeyBJDCWCLMFKKGEE-KXTPALSWSA-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
  • Hemiacetal
  • 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
Water Solubility3.16 g/LALOGPS
logP2.25ALOGPS
logP2.84ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.91 m³·mol⁻¹ChemAxon
Polarizability30.08 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
DarkChem[M+H]+166.59431661259
DarkChem[M-H]-158.46231661259
DeepCCS[M-2H]-203.25530932474
DeepCCS[M+Na]+178.18330932474
AllCCS[M+H]+166.132859911
AllCCS[M+H-H2O]+162.632859911
AllCCS[M+NH4]+169.432859911
AllCCS[M+Na]+170.432859911
AllCCS[M-H]-173.932859911
AllCCS[M+Na-2H]-173.832859911
AllCCS[M+HCOO]-173.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Alpha-dihydroartemisininC[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO43034.8Standard polar33892256
Alpha-dihydroartemisininC[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO41964.9Standard non polar33892256
Alpha-dihydroartemisininC[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO41966.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alpha-dihydroartemisinin,1TMS,isomer #1C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O[Si](C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO42076.0Semi standard non polar33892256
Alpha-dihydroartemisinin,1TBDMS,isomer #1C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO42338.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-dihydroartemisinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-5090000000-2c3d5f82fba0d14e9a072017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-dihydroartemisinin GC-MS (1 TMS) - 70eV, Positivesplash10-009l-9044000000-2064a50503f409cfea9d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-dihydroartemisinin 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 - Alpha-dihydroartemisinin 10V, Positive-QTOFsplash10-000i-0090000000-957508038617389e634a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Positive-QTOFsplash10-000i-0090000000-2f125a25192ab9dac3ff2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Positive-QTOFsplash10-00kf-9120000000-c175280a233f4849aab72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Negative-QTOFsplash10-0019-0090000000-73c4d85a7f84863d34b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Negative-QTOFsplash10-0019-0090000000-03701af12b5b9b5f19d12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Negative-QTOFsplash10-004i-2930000000-61834bfa8e89873f88312017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Positive-QTOFsplash10-000i-0090000000-dac20fbea8167508deeb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Positive-QTOFsplash10-000i-0090000000-844f91982253be80d1352021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Positive-QTOFsplash10-056r-2090000000-acb28e00350215015bd32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Negative-QTOFsplash10-001i-0090000000-1345a6d7d83d2353d1d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Negative-QTOFsplash10-001i-0090000000-4ecf30250c7b7c1b48242021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Negative-QTOFsplash10-053r-1090000000-987e60b5c92178e5b8052021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 Compound456410
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.