4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy}butanoic acid

• ChemBase ID: 160821
• Molecular Formular: C19H28O8
• Molecular Mass: 384.42082
• Monoisotopic Mass: 384.17841786
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@@H](O[C@@H]3O[C@](CC2)(C)OO4)OC(=O)CCC(=O)O)C)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-AHIGJZGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-yl]oxy}butanoic acid
• IUPAC Traditional name: artesunate
• Synonyms: Butanedioic Acid Mono(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] Ester; Artesunic Acid; Artesunate

Database IDs

• CAS Number: 88495-63-0
• PubChem SID: 162254956
• PubChem CID: 6917864

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

Physical Property

• Solubility: Chloroform (Sparingly); DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 132-135°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A777800

Derivative of Artemisinin. Antimalarial.

REFERENCES

• Zhao, Y., et al.: J. Nat. Prod., 49, 139 (1986)
• Lin, A.J., et al.: J. Med. Chem., 30, 2147 (1986)
• Price, R. N., et al.: Expert Opin. Invest. Drugs, 9, 1815 (1986)