(1R,4S,5R,8S,9R,12S)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecan-10-one

• ChemBase ID: 165865
• Molecular Formular: C15H22O4
• Molecular Mass: 266.33278
• Monoisotopic Mass: 266.15180918
• SMILES: [C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)O[C@@H]3O[C@@](CC2)(C)O4)C)C
• Canonical SMILES: C[C@@H]1CC[C@@H]2C34[C@H]1CC[C@](O3)(O[C@H]4OC(=O)[C@@H]2C)C
• InChI: InChI=1S/C15H22O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14+,15?/m1/s1
• InChIKey: ZQGMLVQZBIKKMP-XRNKLDBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,12S)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecan-10-one
• IUPAC Traditional name: (1R,4S,5R,8S,9R,12S)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^4,^1^3.0^8,^1^3]pentadecan-10-one
• Synonyms: (3R,3aS,6R,6aS,9S,10aS,10bR)-Octahydro-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-2(3H)-one; Deoxyarteannuin; Deoxyartemisinin; Deoxyqinghaosu; Desoxyartemisinin; Hydroarteannuin; Qing Hau Sau III; Deoxy Artemisinin

Database IDs

• CAS Number: 72826-63-2
• PubChem SID: 162259998
• PubChem CID: 45038803

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.9298885
• LogD (pH = 7.4): 2.9298885
• Log P: 2.9298885
• Molar Refractivity: 67.6004 cm^3
• Polarizability: 27.62904 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 104-106°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D232150

An analogue of Artemisinin, an antimalarial agent.

REFERENCES

• Mitchell, T., et al.: Clin. Microbiol. Rev., 8, 515 (1995)
• Posner, G., et al.: Bioorg. Med. Chem., 5, 1257 (1995)
• Li, X., et al.: J. Nat. Prod., et al.: 62, 674 (1995)