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

• ChemBase ID: 160817
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: [C@@H]1([C@H]2[C@]3([C@@H](CC1)[C@H]([C@@H](O[C@@H]3OC(=O)C)OC)C)OCC2)C
• Canonical SMILES: CO[C@@H]1O[C@H](OC(=O)C)[C@@]23[C@H]([C@H]1C)CC[C@H]([C@@H]3CCO2)C
• InChI: InChI=1S/C16H26O5/c1-9-5-6-13-10(2)14(18-4)21-15(20-11(3)17)16(13)12(9)7-8-19-16/h9-10,12-15H,5-8H2,1-4H3/t9-,10-,12+,13+,14-,15+,16-/m1/s1
• InChIKey: PJRDDUABDHLSPP-MDVGQMFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S,6R,9S,10R,11R,13R)-11-methoxy-6,10-dimethyl-2,12-dioxatricyclo[7.4.0.0^1,^5]tridecan-13-yl acetate
• IUPAC Traditional name: (1R,5S,6R,9S,10R,11R,13R)-11-methoxy-6,10-dimethyl-2,12-dioxatricyclo[7.4.0.0^1,^5]tridecan-13-yl acetate
• Synonyms: (3aS,4R,6aS,7R,8S,10R,10aR)-Octahydro-8-methoxy-4,7-dimethyl-2H,10H-furo[3,2-i][2]benzopyran-10-ol 10-Acetate,; [3aS-(3aα,4α,6aα,7β,8β,10α,10aS*)]-Octahydro-8-methoxy-4,7-dimethyl-2H,10H-furo[3,2-i][2]benzopyran-10-ol Acetate; Artemether Tetrahydrofuran Acetate

Database IDs

• CAS Number: 181528-64-3
• PubChem SID: 162254952
• PubChem CID: 71313491

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.4769382
• LogD (pH = 7.4): 2.4769382
• Log P: 2.4769382
• Molar Refractivity: 75.4777 cm^3
• Polarizability: 30.903774 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A777415

A metabolite of Artemether (A777400) and derivative of the antimalarial drug Artemisinin (A777500). Studies suggest that it may display neurotoxicity in animals due to its interaction with iron.

REFERENCES

• Smith, S.L. et al.: Neurotoxicology, 19, 557 (1998)
• Blum, W. et al.: J. Chrom. B Biomed. Sci. Appl., 710, 101 (1998)