(1S,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecane

• ChemBase ID: 165864
• Molecular Formular: C17H28O4
• Molecular Mass: 296.40182
• Monoisotopic Mass: 296.19875938
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@@H](O[C@@H]3O[C@](CC2)(C)O4)OCC)C)C
• Canonical SMILES: CCO[C@@H]1O[C@@H]2O[C@@]3(O[C@@]42[C@H]([C@H]1C)CC[C@H]([C@@H]4CC3)C)C
• InChI: InChI=1S/C17H28O4/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,16-,17-/m1/s1
• InChIKey: QNIBYSJOIWYARP-LTLPSTFDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecane
• IUPAC Traditional name: (1S,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecane
• Synonyms: (2S,3R,3aS,6R,6aS,9S,10aR,10bR)-2-Ethoxydecahydro-3,6,9-trimethyl-0aH-9,10b-Epoxypyrano[4,3,2-jk][2]benzoxepin; Chemal 331; Desoxyarteether A; Deoxy Arteether

Database IDs

• CAS Number: 112297-79-7
• PubChem SID: 162259997
• PubChem CID: 71315430

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.6540303
• LogD (pH = 7.4): 3.6540303
• Log P: 3.6540303
• Molar Refractivity: 78.3278 cm^3
• Polarizability: 31.911173 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 68-70°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D232110

A metabolite of Arteether. Artemisinin analogue; antimalarial agent.

REFERENCES

• Klayman, D., et al.: Science, 228, 1049 (1985)
• Avery, M., et al.: Adv. Med. Chem., 4, 125 (1985)
• Avery, M., et al.: J. Med. Chem., 45, 292 (1985)
• Cheng, F., et al.: Bioorg. Med. Chem., 10, 2883 (1985)