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

• ChemBase ID: 160812
• Molecular Formular: C17H28O5
• Molecular Mass: 312.40122
• Monoisotopic Mass: 312.193674
• SMILES: [C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@H]([C@@H](O[C@@H]3O[C@](CC2)(OO4)C)OCC)C)C
• Canonical SMILES: CCO[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/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,16+,17-/m1/s1
• InChIKey: NLYNIRQVMRLPIQ-VBGZEHGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecane
• IUPAC Traditional name: (1S,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecane
• Synonyms: (3R,5aS,6R,8aS,9R,10R,12R,12aR)-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin; [3R-(3α,5aβ,6β,8aβ,9α,10β,12β,12aR*)]-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin; α-Arteether

Database IDs

• CAS Number: 82534-75-6
• PubChem SID: 162254947
• PubChem CID: 9818237

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.8382
• LogD (pH = 7.4): 3.8382
• Log P: 3.8382
• Molar Refractivity: 79.4091 cm^3
• Polarizability: 32.631 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A774295

The diastereomer of Arteether, a potent antimalarial drug.

REFERENCES

• Li, Y., et al.: Acta Pharm. Sin., 16, 429 (1981)
• Brossi, A., et al.: J. Med. Chem., 31, 645 (1981)
• Grace, J., et al.: Drug Metab. Dispos. 26, 313 (1981)
• Cheng, F., et al.: Bioorg. Med. Chem., 10, 2883 (1981)