(1S,4S,5R,8S,9R,12R)-11-(2-hydroxyethyl)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

• ChemBase ID: 170537
• Molecular Formular: C17H27NO5
• Molecular Mass: 325.39998
• Monoisotopic Mass: 325.18892297
• SMILES: [C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)N([C@@H]3O[C@@](CC2)(C)OO4)CCO)C)C
• Canonical SMILES: OCCN1C(=O)[C@H](C)[C@H]2C34[C@H]1O[C@](C)(CC[C@H]4[C@@H](CC2)C)OO3
• InChI: InChI=1S/C17H27NO5/c1-10-4-5-13-11(2)14(20)18(8-9-19)15-17(13)12(10)6-7-16(3,21-15)22-23-17/h10-13,15,19H,4-9H2,1-3H3/t10-,11-,12+,13+,15-,16+,17?/m1/s1
• InChIKey: JXNUXFXHWUZMGM-XXVBWMPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8S,9R,12R)-11-(2-hydroxyethyl)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (1S,4S,5R,8S,9R,12R)-11-(2-hydroxyethyl)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• Synonyms: (3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-11-(2-hydroxyethyl)-3,6,9-trimethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one; N-(2-Hydroxyethyl)-11-azaartemisinin

Database IDs

• CAS Number: 255731-00-1
• PubChem SID: 164226447
• PubChem CID: 71749019

CALCULATED PROPERTIES

• Acid pKa: 15.569261
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.9184712
• LogD (pH = 7.4): 1.9184715
• Log P: 1.9184715
• Molar Refractivity: 81.8205 cm^3
• Polarizability: 33.105534 Å^3
• Polar Surface Area: 68.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941970

A derivative of 11-Azaartemisinin which showed a high order of activity against multidrug-resistant malaria by oral route.

REFERENCES

• Meshnick, S.R., et al.: Microbiol. Rev., 60, 301 (1996)
• O’Neill, P.M., et al.: J. Med. Chem., 45, 1052 (1996)
• Rottmann, M., et al.: J. Med. Chem., 51, 1035 (1996)