(1R,4S,5R,8S,9R,10S,12R,13R)-9-(13C,2H3)methyl-1,5-dimethyl(10-2H)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

• ChemBase ID: 167515
• Molecular Formular: C15H24O5
• Molecular Mass: 285.34071484
• Monoisotopic Mass: 285.16572871
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@H](O[C@@H]3O[C@@](CC2)(OO4)C)O)[13CH3])C
• Canonical SMILES: O[C@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1[13CH3])CC[C@H]4C)OO3
• InChI: InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1/i2+1
• InChIKey: BJDCWCLMFKKGEE-JQHCJWICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,10S,12R,13R)-9-(^1^3C,^2H₃)methyl-1,5-dimethyl(10-^2H)-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-ol
• IUPAC Traditional name: (1R,4S,5R,8S,9R,10S,12R,13R)-9-(^1^3C,^2H₃)methyl-1,5-dimethyl(10-^2H)-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-ol
• Synonyms: β-Dihydroartemisinin-13C,d4; Alaxin-13C,d4; Cotecxin-13C,d4; Cotexin-13C,d4; DHQHS 2-13C,d4; Dihydroartemisinine-13C,d4; Dihydroqinghaosu-13C,d4; Dihydro Artemisinin-13C,d4; (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol-13C,d4

Database IDs

• PubChem SID: 162261648
• PubChem CID: 71316127

CALCULATED PROPERTIES

• Acid pKa: 12.114969
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.8382654
• LogD (pH = 7.4): 2.838257
• Log P: 2.8382654
• Molar Refractivity: 69.9093 cm^3
• Polarizability: 28.899292 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448363

The labelled analogue of the main metabolite of Artemisinin, Arteether, Artemether, Artesunate. An active antimalarial metabolite.

REFERENCES

• de Vries, P., et al.: Drugs, 52, 818 (1996)
• Kamolrat, S., et al.: Antimicrob. Agents Chemother., 47, 3795 (1996)
• Mithwani, S., et al.: Br. J. Clin. Pharmacol., 57, 146 (1996)