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

• ChemBase ID: 159728
• Molecular Formular: C15H24N2O4
• Molecular Mass: 296.36206
• Monoisotopic Mass: 296.17360726
• SMILES: [C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)N([C@@H]3O[C@@](CC2)(C)OO4)N)C)C
• Canonical SMILES: O=C1N(N)[C@@H]2O[C@]3(C)CC[C@@H]4C2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: InChI=1S/C15H24N2O4/c1-8-4-5-11-9(2)12(18)17(16)13-15(11)10(8)6-7-14(3,19-13)20-21-15/h8-11,13H,4-7,16H2,1-3H3/t8-,9-,10+,11+,13-,14+,15?/m1/s1
• InChIKey: SDPLWYWNQUROTR-XRNKLDBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,12R)-11-amino-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)-11-amino-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)-11-Aminodecahydro-3,6,9-trimethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one; N-Amino-11-azaartemisinin

Database IDs

• CAS Number: 1086409-78-0
• PubChem SID: 162253863
• PubChem CID: 71313112

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0815046
• LogD (pH = 7.4): 2.088334
• Log P: 2.0884218
• Molar Refractivity: 75.1156 cm^3
• Polarizability: 30.21687 Å^3
• Polar Surface Area: 74.02 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A583700

A derivative of 11-Azaartemisinin which showed a high order of activity against multidrug-resistant malaria by oral route.

REFERENCES

• Meshnick, S.R., et al.: Microbiol. Rev., 60, 301 (1996)
• O’Neill, P.M., et al.: J. Med. Chem., 45, 1052 (1996)
• Rottmann, M., et al.: J. Med. Chem., 51, 1035 (1996)