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COCONUT Compound

Artesunate

CNP0334140.1 · C19H28O8 · View on COCONUT ↗

2D Structure

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Identifiers

NameArtesunate
IUPAC Name4-oxo-4-[[(1~{R},4~{S},5~{R},8~{S},9~{R},10~{S},12~{R},13~{R})-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy]butanoic acid
COCONUT IDCNP0334140.1
CAS88495-63-0
InChIKeyFIHJKUPKCHIPAT-AHIGJZGOSA-N
InChIInChI=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
SMILESC[C@H]1[C@H](OC(=O)CCC(=O)O)O[C@@H]2O[C@@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3

Properties

Molecular FormulaC19H28O8
Molecular Weight384.43
Exact Mass384.17842
Log P (ALogP)2.60
TPSA100.52
H-Bond Donors / Acceptors1 / 7
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.58
NP-likeness3.15

Classification

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

Reported in GR-MAPs Plants

Artemisia annua as “Artemisia annua L.” in COCONUT

References (13)

  1. 10.1016/j.bmcl.2017.07.039
  2. 10.1021/ACS.JNATPROD.8B00956
  3. 10.1021/acs.jnatprod.0c00245
  4. 10.1021/acs.jnatprod.5b00581
  5. 10.1021/acs.jnatprod.6b00759
  6. 10.1021/acs.jnatprod.7b00587
  7. 10.1021/acs.jnatprod.7b00876
  8. 10.1021/acs.jnatprod.7b00992
  9. 10.1021/acs.jnatprod.8b00154
  10. 10.1021/acs.jnatprod.8b00956
  11. 10.1021/acs.jnatprod.9b00721
  12. 10.1021/acs.jnatprod.9b00933
  13. 10.1371/JOURNAL.PONE.0080790

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.