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

• ChemBase ID: 170430
• Molecular Formular: C15H24O5
• Molecular Mass: 284.34806
• Monoisotopic Mass: 284.16237387
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H](C(O[C@@H]3O[C@]([C@@H](C2)O)(O4)C)O)C)C
• Canonical SMILES: OC1O[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/C15H24O5/c1-7-4-5-9-8(2)12(17)18-13-15(9)10(7)6-11(16)14(3,19-13)20-15/h7-13,16-17H,4-6H2,1-3H3/t7-,8-,9+,10+,11-,12?,13-,14+,15+/m1/s1
• InChIKey: HTYSVFNZNVQCLV-PBDCUWOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecane-2,10-diol
• IUPAC Traditional name: (1R,2R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecane-2,10-diol
• Synonyms: (3R,3aS,6R,6aS,8R,9S,10aR,10bR)-Decahydro-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-2,8-diol; 3-Hydroxy Desoxy-dihydroartemisinin; 3-Hydroxy Deoxy Dihydro Artemisinin

Database IDs

• CAS Number: 126641-61-0
• PubChem SID: 164226340
• PubChem CID: 15227255

CALCULATED PROPERTIES

• Acid pKa: 12.083721
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.8078936
• LogD (pH = 7.4): 1.8078848
• Log P: 1.8078938
• Molar Refractivity: 70.0791 cm^3
• Polarizability: 28.830023 Å^3
• Polar Surface Area: 68.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H934950

A metabolte of the antimalarial endoperoxide Dihydroartemisinin (D448360).

REFERENCES

• Maggs, J. et al.: Drug Metab. Dispos., 25, 1200 (1997)
• Idowu, O.R. et al.: Pharmac. Res., 14, 1449 (1997)