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COCONUT Compound

Artemisinine

CNP0216348.1 · C15H22O5 · View on COCONUT ↗

2D Structure

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Identifiers

NameArtemisinine
IUPAC Name(1~{S},4~{S},5~{R},8~{S},9~{R},12~{S},13~{R})-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-one
COCONUT IDCNP0216348.1
CAS63968-64-9
InChIKeyBLUAFEHZUWYNDE-DKGJTOOQSA-N
InChIInChI=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
SMILESC[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4

Properties

Molecular FormulaC15H22O5
Molecular Weight282.34
Exact Mass282.14672
Log P (ALogP)2.39
TPSA53.99
H-Bond Donors / Acceptors0 / 5
Rotatable Bonds0
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.50
NP-likeness3.84

Classification

NP PathwayTerpenoids
NP SuperclassSesquiterpenoids
NP ClassArteminisin
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTerpene lactones

Reported in GR-MAPs Plants

Artemisia annua as “Artemisia annua L.” in COCONUT

References (10)

  1. 10.1016/j.bmc.2007.07.032
  2. 10.1021/NP5002863
  3. 10.1021/acs.jnatprod.5b00187
  4. 10.1021/np0400095
  5. 10.1021/np0702133
  6. 10.1021/np400908u
  7. 10.1021/np5002863
  8. 10.1021/np50034a027
  9. 10.1021/np50098a017
  10. 10.1021/np9605246

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.