(1R,5S,6R,9S,10R,13R)-11-hydroxy-6,10-dimethyl-2,12-dioxatricyclo[7.4.0.01,5]tridecan-13-yl acetate

• ChemBase ID: 167517
• Molecular Formular: C15H24O5
• Molecular Mass: 284.34806
• Monoisotopic Mass: 284.16237387
• SMILES: [C@@H]1([C@H]2[C@]3([C@@H](CC1)[C@H](C(O[C@@H]3OC(=O)C)O)C)OCC2)C
• Canonical SMILES: CC(=O)O[C@H]1OC(O)[C@@H]([C@H]2[C@]31OCC[C@H]3[C@H](C)CC2)C
• InChI: InChI=1S/C15H24O5/c1-8-4-5-12-9(2)13(17)20-14(19-10(3)16)15(12)11(8)6-7-18-15/h8-9,11-14,17H,4-7H2,1-3H3/t8-,9-,11+,12+,13?,14+,15-/m1/s1
• InChIKey: MXTIBMLCXHSHGJ-AAAPMNIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S,6R,9S,10R,13R)-11-hydroxy-6,10-dimethyl-2,12-dioxatricyclo[7.4.0.0^1,^5]tridecan-13-yl acetate
• IUPAC Traditional name: (1R,5S,6R,9S,10R,13R)-11-hydroxy-6,10-dimethyl-2,12-dioxatricyclo[7.4.0.0^1,^5]tridecan-13-yl acetate
• Synonyms: Dihydro Artemisinin Tetrahydrofuran Acetate; (3aS,4R,6aS,7R,10R,10aR)-octahydro-4,7-dimethyl-2H,10H-furo[3,2-i]-2-benzopyran-8,10-diol 10-Acetate; Dihydroartemisinin Furano Acetate; (3aS,4R,6aS,7R,10R,10aR)-Octahydro-4,7-dimethyl-2H,10H-furo[3,2-i][2]benzopyran-8,10-diol 10-Acetate

Database IDs

• CAS Number: 198817-95-7
• PubChem SID: 162261650
• PubChem CID: 71316129

CALCULATED PROPERTIES

• Acid pKa: 12.11481
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8338116
• LogD (pH = 7.4): 1.8338034
• Log P: 1.8338118
• Molar Refractivity: 70.7265 cm^3
• Polarizability: 29.003351 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448375

A metabolite of Artemisinin (A777500).

REFERENCES

• Idowu, O.R. et al.: Pharmac. Res., 14, 1449 (1997)