4-oxo-4-{[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid

• ChemBase ID: 72921
• Molecular Formular: C19H28O8
• Molecular Mass: 384.42082
• Monoisotopic Mass: 384.17841786
• SMILES: [C@@H]12[C@@]34[C@@H](CC[C@H]1C)[C@H]([C@H](O[C@@H]3O[C@](CC2)(OO4)C)OC(=O)CCC(=O)O)C
• Canonical SMILES: OC(=O)CCC(=O)O[C@H]1O[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/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
• InChIKey: FIHJKUPKCHIPAT-HXMLZIBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4-{[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid
• IUPAC Traditional name: 4-oxo-4-{[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid
• Synonyms: Artesunate

Database IDs

• CAS Number: 88495-63-0
• PubChem SID: 162037841
• PubChem CID: 156252

CALCULATED PROPERTIES

• Acid pKa: 3.768143
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.3712845
• LogD (pH = 7.4): -0.17246954
• Log P: 3.1042538
• Molar Refractivity: 89.9541 cm^3
• Polarizability: 37.044033 Å^3
• Polar Surface Area: 100.52 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2265

Research Area: Infection
Biological Activity:
Artesunate is a part of the artemisinin group of agents with an IC50 of < 5 μM for small cell lung carcinoma cell line H69. Artesunate is a semi-synthetic derivative of artemisinin that is water-soluble and may therefore be given by injection. Artesunate is used primarily as treatment for malaria; but artesunate has also been shown to be >90% efficacious at reducing egg production in Schistosoma haematobium infection. [1][2]

REFERENCES

• Boulanger D et al. Trans R Soc Trop Med Hyg. 2007 Feb;101(2):113-6.