Structure Database (LMSD)

Common Name
Artemisinin
Systematic Name
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
Synonyms
  • Arteannuin
  • Huanghuahaosu
LM ID
LMPR0103190003
Formula
Exact Mass
Calculate m/z
282.146725
Status
Curated



Classification

Biological Context

Artemisinin is an antimalarial agent with anticancer activity.1,2 It is an iron(II) oxide-reactive endoperoxide that generates reactive oxygen species (ROS) upon cleavage of its endoperoxide bridge.3 It reduces the growth of various P. falciparum strains in vitro (IC50s = 3.98-20.36 nM) and reduces parasitemia in mice infected with P. falciparum with a curative dose (CD50) value of 140 mg/kg.1,4 It also reduces P. berghei infection in mice (ED50 = 5.6 mg/kg per day).5 Artemisinin (100-400 μM) induces cell cycle arrest in the G0/G1 phase and apoptosis and inhibits growth of SK-N-AS, BE(2)-C, SK-N-DZ, and SHEP1 neuroblastoma cells in a time- and concentration-dependent manner.2 It also suppresses BE(2)-C cell colony formation in a soft agar assay and reduces tumor growth in a BE(2)-C mouse xenograft model. Formulations containing artemisinin have been used in combination therapies for the treatment of malaria.

This information has been provided by Cayman Chemical

References

1. Chawira, A.N., Warhurst, D.C., Robinson, B.L., et al. The effect of combinations of qinghaosu (artemisinin) with standard antimalarial drugs in the suppressive treatment of malaria in mice. Trans. R. Soc. Trop. Med. Hyg. 81(4), 554-558 (1987).
4. Ooko, E., Saeed, M.E.M., Kadioglu, O., et al. Artemisinin derivatives induce iron-dependent cell death (ferroptosis) in tumor cells. Phytomedicine 22(11), 1045-1054 (2015).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Artemisia annua (#35608)
Magnoliopsida (#3398)
Structure and reaction of arteannuin

String Representations

InChiKey (Click to copy)
BLUAFEHZUWYNDE-NNWCWBAJSA-N
InChi (Click to copy)
InChI=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
SMILES (Click to copy)
[C@@]123OO[C@@]4(CC[C@@]1([H])[C@@H](CC[C@@]2([H])[C@H](C(=O)O[C@]3([H])O4)C)C)C

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 5
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 256.13
Topological Polar Surface Area 62.27
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 5
logP 3.25
Molar Refractivity 69.58

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Created at
-
Updated at
2nd Aug 2024