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
3D model of Artemisinin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
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
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
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