Artemisinin (CHEM017564)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:57 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017564
Identification
Common NameArtemisinin
ClassSmall Molecule
DescriptionA sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,5,9-Trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-oneChEBI
ArteannuinChEBI
ArtemisininaChEBI
ArtemisinineChEBI
ArtemisininumChEBI
HuanghuahaosuChEBI
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-J)-1,2-benzodioxepin-10(3H)-oneChEBI
QHSChEBI
Qing hau sauChEBI
QinghaosuChEBI
Quing hau sauChEBI
QuinghaosuMeSH
ArtemisininChEBI
Chemical FormulaC15H22O5
Average Molecular Mass282.336 g/mol
Monoisotopic Mass282.147 g/mol
CAS Registry Number63968-64-9
IUPAC Name(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one
Traditional Name(+)-artemisinin
SMILES[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4
InChI IdentifierInChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
InChI KeyBLUAFEHZUWYNDE-NNWCWBAJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Artemisinin skeleton
  • Terpene lactone
  • Sesquiterpenoid
  • Delta valerolactone
  • Delta_valerolactone
  • Oxepane
  • Oxane
  • 1,2,4-trioxane
  • Carboxylic acid ester
  • Lactone
  • Dialkyl peroxide
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP2.52ALOGPS
logP3.11ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.68 m³·mol⁻¹ChemAxon
Polarizability29.43 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0007-0901000000-4fa10fe72dc24b85ac9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0190000000-3391c971e951545100eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ldj-0960000000-ff3a9e18db5c8c53bcb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01wb-0910000000-42c2b516c8462b3dd492Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01x1-0900000000-5c3e44b5d52be3adbba2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a7l-0900000000-01583256dc6d13c1315fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-0900000000-189290ae52e9283563baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-81624c4cf74214fdaa9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1090000000-280b3ca0132072b52506Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9100000000-73e8efda73cc4b76c149Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0090000000-f9b1c888e060cd130d8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-1090000000-53e88c0fa4a2405b229cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4690000000-687f2a3a4ca745522896Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13132
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003359
BiGG IDNot Available
BioCyc IDCPD-7561
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArtemisinin
Chemspider IDNot Available
ChEBI ID223316
PubChem Compound ID68827
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15330155
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18008167
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19090980
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22174561
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7877142
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8544181