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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2018-04-09 20:47:50 UTC
Update Date2022-03-07 03:18:15 UTC
HMDB IDHMDB0240267
Secondary Accession NumbersNone
Metabolite Identification
Common NameArtesunate
DescriptionArtesunate, also known as artesunic acid or AS, 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. Based on a literature review a significant number of articles have been published on Artesunate.
Structure
Data?1563892740
Synonyms
ValueSource
ArtesunatoChEBI
ArtesunatumChEBI
Artesunic acidChEBI
ASChEBI
Butanedioic acid, 1-[(3R,5as,6R,8as,9R,10S,12R,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-J]-1,2-benzodioxepin-10-yl] esterChEBI
Dihydroqinghasu hemsuccinateChEBI
Butanedioate, 1-[(3R,5as,6R,8as,9R,10S,12R,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-J]-1,2-benzodioxepin-10-yl] esterGenerator
Dihydroqinghasu hemsuccinic acidGenerator
MalartinHMDB
Dihydroartemisinine-12-alpha-succinateHMDB
Dihydroartemisinin, succinylHMDB
Succinyl dihydroartemisininHMDB
MalacefHMDB
Sodium artesunateHMDB
Dihydroartemisinine 12 alpha succinateHMDB
Chemical FormulaC19H28O8
Average Molecular Weight384.425
Monoisotopic Molecular Weight384.178417862
IUPAC Name4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid
Traditional Name4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid
CAS Registry Number88495-63-0
SMILES
[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O4
InChI Identifier
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
InChI KeyFIHJKUPKCHIPAT-AHIGJZGOSA-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
  • Fatty acid ester
  • Heterocyclic fatty acid
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Oxane
  • Fatty acyl
  • 1,2,4-trioxane
  • Carboxylic acid ester
  • Dialkyl peroxide
  • Oxacycle
  • Carboxylic acid
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
logP2.35ALOGPS
logP3.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.95 m³·mol⁻¹ChemAxon
Polarizability39.48 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
AllCCS[M-H]-191.81231661259
AllCCS[M+H]+189.51231661259
DeepCCS[M-2H]-220.81430932474
DeepCCS[M+Na]+194.83430932474
AllCCS[M+H]+189.532859911
AllCCS[M+H-H2O]+187.032859911
AllCCS[M+NH4]+191.832859911
AllCCS[M+Na]+192.532859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-192.232859911
AllCCS[M+HCOO]-192.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artesunate[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O44159.3Standard polar33892256
Artesunate[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O42591.2Standard non polar33892256
Artesunate[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O42695.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artesunate,1TMS,isomer #1C[C@@H]1CC[C@H]2[C@@H](C)[C@H](OC(=O)CCC(=O)O[Si](C)(C)C)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO42722.7Semi standard non polar33892256
Artesunate,1TBDMS,isomer #1C[C@@H]1CC[C@H]2[C@@H](C)[C@H](OC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO42968.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artesunate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artesunate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artesunate GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artesunate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artesunate GC-MS ("Artesunate,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 10V, Positive-QTOFsplash10-00kr-2459000000-709f5cba7340e7cb08022017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 20V, Positive-QTOFsplash10-014i-7392000000-6aade85a0d3ce77db50e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 40V, Positive-QTOFsplash10-0a4l-9050000000-c432eeabf339e3f7593b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 10V, Negative-QTOFsplash10-000t-9034000000-4fd3316b534c1c9695e52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 20V, Negative-QTOFsplash10-00m0-4191000000-c1b630ac82bbe1ed3eec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 40V, Negative-QTOFsplash10-0a4i-8590000000-1aec7778a60c3c83b96f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 10V, Positive-QTOFsplash10-000i-0059000000-c401777b25dc78e3e3d62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 20V, Positive-QTOFsplash10-014r-5091000000-a70049f2a7891ca11fda2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 40V, Positive-QTOFsplash10-0a4u-9040000000-7170837027905000882c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 10V, Negative-QTOFsplash10-001i-0094000000-8eadce9bbd79f81901642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 20V, Negative-QTOFsplash10-0089-9072000000-f24fb27ab8342500be332021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artesunate 40V, Negative-QTOFsplash10-0ab9-9010000000-bde61be07af13e719ef62021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09274
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5293084
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArtesunate
METLIN IDNot Available
PubChem Compound6917864
PDB IDNot Available
ChEBI ID63918
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1481341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available