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

• ChemBase ID: 160820
• Molecular Formular: C15H20O5
• Molecular Mass: 280.3163
• Monoisotopic Mass: 280.13107374
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)C(=C)C(=O)O[C@@H]3O[C@](CC2)(C)OO4)C
• Canonical SMILES: O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H](C1=C)CC[C@H]4C)OO3
• InChI: InChI=1S/C15H20O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1
• InChIKey: IGEBZMMCKFUABB-KPHNHPKPSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 101020-89-7
• PubChem SID: 162254955
• PubChem CID: 11000442

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.2557127
• LogD (pH = 7.4): 3.2557127
• Log P: 3.2557127
• Molar Refractivity: 68.4851 cm^3
• Polarizability: 28.111227 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A777550

Artemisitene, the oxidized form of Artemisinin (A777500), exists as a minor constituent in an American variant of Artemisia annua. Artemisinin precursors are the important basic substances for biosynthesis of Artemisinin, including Artemisinic acid, Artem

REFERENCES

• Li, Y., et al.: Curr. Med. Chem., 10, 2197 (2003)
• Marrero-Ponce, Y., et al.: Bioorg. Med. Chem., 13, 1293 (2003)
• McMichael, A., et al.: Lancet, 367, 859 (2003)