(1S,2R,4S,5R,8S,9R,10R,12S,13R)-10-methoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecan-2-ol

• ChemBase ID: 170449
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@@H](O[C@H]3O[C@@]([C@@H](C2)O)(O4)C)OC)C)C
• Canonical SMILES: CO[C@@H]1O[C@H]2O[C@@]3(O[C@@]42[C@H]([C@H]1C)CC[C@H]([C@@H]4C[C@H]3O)C)C
• InChI: InChI=1S/C16H26O5/c1-8-5-6-10-9(2)13(18-4)19-14-16(10)11(8)7-12(17)15(3,20-14)21-16/h8-14,17H,5-7H2,1-4H3/t8-,9-,10+,11+,12-,13-,14+,15-,16+/m1/s1
• InChIKey: NYMSZZKRBMNKGP-YMSVXTLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4S,5R,8S,9R,10R,12S,13R)-10-methoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecan-2-ol
• IUPAC Traditional name: (1S,2R,4S,5R,8S,9R,10R,12S,13R)-10-methoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecan-2-ol
• Synonyms: (2S,3R,3aS,6R,6aS,8R,9S,10aR,10bR)-Decahydro-2-methoxy-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-8-ol; 3α-Hydroxydeoxyartemether; [2S-(2α,3α,3aβ,6β,6aβ,8β,9β,10aα,10bβ)]-Decahydro-2-methoxy-3,6,9-trimethyl-10aH-9,10b-Epoxypyrano[4,3,2-jk][2]benzoxepin-8-ol; 3α-Hydroxydesoxy Artemether

Database IDs

• CAS Number: 174097-70-2
• PubChem SID: 164226359
• PubChem CID: 71748978

CALCULATED PROPERTIES

• Acid pKa: 13.239188
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.4510202
• LogD (pH = 7.4): 2.4510198
• Log P: 2.4510202
• Molar Refractivity: 74.8303 cm^3
• Polarizability: 30.729315 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H939050

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)
• Abourashed, E.A. et al.: J. Natur. Prod., 59, 251 (1998)