(1S,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

• ChemBase ID: 167513
• 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@@](CC2)(C)OO4)O)C)C
• Canonical SMILES: OC1O[C@@H]2O[C@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)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
• InChIKey: BJDCWCLMFKKGEE-SUZORCHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-ol
• IUPAC Traditional name: (1S,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-ol
• Synonyms: (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; β-Dihydroartemisinin; Alaxin; Cotecxin; Cotexin; DHQHS 2; Dihydroartemisinine; Dihydroqinghaosu; Dihydro Artemisinin

Database IDs

• CAS Number: 71939-50-9
• PubChem SID: 162261646
• PubChem CID: 11832956

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

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 144-149°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D448360

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)