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

• ChemBase ID: 160907
• Molecular Formular: C15H23NO4
• Molecular Mass: 281.34742
• Monoisotopic Mass: 281.16270822
• SMILES: [C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)N[C@@H]3O[C@@](CC2)(C)OO4)C)C
• Canonical SMILES: O=C1N[C@@H]2O[C@]3(C)CC[C@@H]4C2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: InChI=1S/C15H23NO4/c1-8-4-5-11-9(2)12(17)16-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3,(H,16,17)/t8-,9-,10+,11+,13-,14+,15?/m1/s1
• InChIKey: LSHOKYZGSIIBMK-XRNKLDBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,12R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (1S,4S,5R,8S,9R,12R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• Synonyms: (3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one; (-)-11-Azaartemisinin; 11-Azaartemisinin

Database IDs

• CAS Number: 162791-23-3
• PubChem SID: 162255042
• PubChem CID: 71313537

CALCULATED PROPERTIES

• Acid pKa: 10.632575
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3848944
• LogD (pH = 7.4): 2.3846724
• Log P: 2.3848975
• Molar Refractivity: 70.6315 cm^3
• Polarizability: 28.783083 Å^3
• Polar Surface Area: 56.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A794900

A nontoxic analog of Artemisinin for the oral treatment of malaria.

REFERENCES

• Klayman, D., et al.: Science, 228, 1049 (1985)
• Hu, Y., et al.: Bioorg. Chem., 20, 148 (1985)
• Avery, M., et al.: J. Med. Chem., 36, 4264 (1985)
• Meshnick, S., et al.: Antimicrob. Agents Chemother., 37, 1108 (1985)
• Grace, J., et al.: Xenobiotica, 29, 703