(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-ene

• ChemBase ID: 160660
• Molecular Formular: C15H22O4
• Molecular Mass: 266.33278
• Monoisotopic Mass: 266.15180918
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)C(=CO[C@@H]3O[C@@](CC2)(OO4)C)C)C
• Canonical SMILES: C[C@@H]1CC[C@@H]2[C@@]34[C@H]1CC[C@@](OO3)(O[C@H]4OC=C2C)C
• InChI: InChI=1S/C15H22O4/c1-9-4-5-11-10(2)8-16-13-15(11)12(9)6-7-14(3,17-13)18-19-15/h8-9,11-13H,4-7H2,1-3H3/t9-,11+,12+,13-,14-,15+/m1/s1
• InChIKey: UKXCIQFCSITOCY-VLDCTWHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadec-9-ene
• IUPAC Traditional name: (1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadec-9-ene
• Synonyms: (3R,5aS,6R,8aS,12R,12aR)-3,4,5,5a,6,7,8,8a-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin; (+)-9,10-Anhydrodehydroartemisinin; 9,10-Anhydro-10-deoxoartemisinin; 9,10-Anhydrodehydroartemisinin; Anhydrodihydroartemisinin; Anhydrodihydroartemisnin; Anhydro Dihydro Artemisinin

Database IDs

• CAS Number: 82596-30-3
• PubChem SID: 162254795
• PubChem CID: 393517

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.2072077
• LogD (pH = 7.4): 3.2072077
• Log P: 3.2072077
• Molar Refractivity: 68.7277 cm^3
• Polarizability: 27.99468 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637875

Anhydrodihydroartemisinin is a semisynthetic derivative of Artersiminin (A777500). Anhydrodihydroartemisinin is a decomposition product of Artesunate (A777800) and Dihydroartemisinin (D448360). Anhydrodihydroartemisinin showed antimalarial activity althou

REFERENCES

• Haynes, R.K. et al.: ChemMedChem, 2, 1448 (2007)
• Lin, A.J. et al.: Am. J. Trop. Med. Hyg., 50, 777 (2007)
• Galal, A. et al.: J. Nat. Prod., 68, 1274 (2007)