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

• ChemBase ID: 160819
• Molecular Formular: C15H22O5
• Molecular Mass: 282.33218
• Monoisotopic Mass: 282.1467238
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@@H](C(=O)O[C@@H]3O[C@](CC2)(C)OO4)C)C
• Canonical SMILES: O=C1O[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/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9+,10+,11+,13-,14-,15-/m1/s1
• InChIKey: BLUAFEHZUWYNDE-DWIPZSBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• Synonyms: (3R,5aS,6R,8aS,9S,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one; (+)-9-Epiartemisinin; 11-epi-Artemisinin; 9-epi-Artemisinin

Database IDs

• CAS Number: 113472-97-2
• PubChem SID: 162254954
• PubChem CID: 821423

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.114058
• LogD (pH = 7.4): 3.114058
• Log P: 3.114058
• Molar Refractivity: 68.6817 cm^3
• Polarizability: 28.359936 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A777505

A chiral isomer of Artemisinin (A777500), an antimalarial. A metabolite of Artemisitene (A777550).

REFERENCES

• Orabi, K.Y. et al.: Phytochem., 51, 257 (1999)
• Jefford, C.W. et al.: Helv. Chim. Acta, 83, 1239 (1999)
• Klayman, D.L., et al.: Science, 228, 1049 (1985;