(1R,4S,5R,8S,9R,10R,12R,13R)-10-(2H3)methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane

• ChemBase ID: 160816
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@@H](O[C@@H]3O[C@@](CC2)(OO4)C)OC)C)C
• Canonical SMILES: CO[C@@H]1O[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/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13-,14-,15-,16-/m1/s1
• InChIKey: SXYIRMFQILZOAM-CNNNLJIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,10R,12R,13R)-10-(^2H₃)methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecane
• IUPAC Traditional name: (1R,4S,5R,8S,9R,10R,12R,13R)-10-(^2H₃)methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecane
• Synonyms: α-Artemether-d3; (+)-α-Artemether-d3; SM 229-d3; α-Artemether-d3; α-Dihydroartemisinin Μethyl-d3 Εther; (3R,5aS,6R,8aS,9R,10R,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-d3

Database IDs

• PubChem SID: 162254951
• PubChem CID: 71313490

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.481392
• LogD (pH = 7.4): 3.481392
• Log P: 3.481392
• Molar Refractivity: 74.6605 cm^3
• Polarizability: 30.79904 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A777412

Labelled Derivative of Artemisinin (A777500). Shows antimalarial and antifungal activity.

REFERENCES

• Michael, O., et al.: Malaria J., 9, 335 (2010)
• Cesar, I., et al.: J. Pharm. Biomed. Anal., 54, 114 (2010)
• Galal, A. et al.: J. Nat. Prod. 68, 1274 (2005)