(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

• ChemBase ID: 125947
• Molecular Formular: C15H22O5
• Molecular Mass: 282.33218
• Monoisotopic Mass: 282.1467238
• SMILES: O=C1O[C@@H]2O[C@@]3(OO[C@]42[C@@H](CC3)[C@H](C)CC[C@H]4[C@H]1C)C
• Canonical SMILES: O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: 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
• InChIKey: BLUAFEHZUWYNDE-NNWCWBAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (+)-artemisinin
• Synonyms: (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epox12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one; Artemisine; Arteannuin; Huanghuahaosu; QHS; Artemisinine; Qinghaosu; Artemisinin

Database IDs

• CAS Number: 63968-64-9
• PubChem SID: 162220290
• PubChem CID: 68827
• CHEBI ID: 223316
• ATC CODE: P01BE01
• CHEMBL: 77
• Chemspider ID: 62060
• KEGG ID: D02481
• Unique Ingredient Identifier: 9RMU91N5K2
• Wikipedia Title: Artemisinin

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.114058
• LogD (pH = 7.4): 3.114058
• Log P: 3.114058
• Molar Refractivity: 68.6817 cm^3
• Polarizability: 28.359936 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 152-157 °C (305.6-314.6°F); 156-157°C
• Density: 1.24 ± 0.1 g/cm^3

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral

DETAILS

Toronto Research Chemicals - A777500

Active antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial.

REFERENCES

• Klayman, D.L., et al.: Science, 228, 1049 (1985)
• Price, R.N., et al.: Expert Opin. Invest. Drugs, 9, 1815 (1985)
• Meshnick, S.R., et al.: Int. J., Parasitol., 32, 1655 (1985)