(3aS,4S,7R,9R,10R,11R,13R,15R,15aR)-10-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-{4-[4-(pyridin-3-yl)-1H-imidazol-1-yl]butyl}-tetradecahydro-1H-oxacyclotetradeca[4,3-d][1,3]oxazole-2,6,8,14-tetrone

• ChemBase ID: 178118
• Molecular Formular: C43H65N5O10
• Molecular Mass: 812.0037
• Monoisotopic Mass: 811.47314331
• SMILES: [C@H]1([C@H](C(=O)[C@@H](C(=O)O[C@H]([C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]1(C)OC)C)C)N(C(=O)O2)CCCCn1cc(nc1)c1cccnc1)C)CC)C)C)O[C@H]1[C@H]([C@H](C[C@@H](O1)C)N(C)C)O
• Canonical SMILES: CC[C@@H]1OC(=O)[C@@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)C[C@@H]([C@@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
• InChI: InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33+,36-,37-,38-,40+,42-,43-/m1/s1
• InChIKey: LJVAJPDWBABPEJ-WMHCQVJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,4S,7R,9R,10R,11R,13R,15R,15aR)-10-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-{4-[4-(pyridin-3-yl)-1H-imidazol-1-yl]butyl}-tetradecahydro-1H-oxacyclotetradeca[4,3-d][1,3]oxazole-2,6,8,14-tetrone
• IUPAC Traditional name: (3aS,4S,7R,9R,10R,11R,13R,15R,15aR)-10-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-{4-[4-(pyridin-3-yl)imidazol-1-yl]butyl}-octahydrooxacyclotetradeca[4,3-d][1,3]oxazole-2,6,8,14-tetrone
• Synonyms: (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyloctahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-2H-oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)tetrone; Ketek; Telithromycin 90%

Database IDs

• CAS Number: 191114-48-4
• PubChem SID: 164234028
• PubChem CID: 71752343

CALCULATED PROPERTIES

• Acid pKa: 8.8389635
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): 3.0678577
• LogD (pH = 7.4): 5.113476
• Log P: 5.367185
• Molar Refractivity: 214.6835 cm^3
• Polarizability: 86.46801 Å^3
• Polar Surface Area: 171.85 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 88-91°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T016500

A ketolide antibiotic, used to treat respiratory infections

REFERENCES

• Lee, J., et al.: Pulmonary Pharmacology & Therapeutics, 21, 860 (2008)
• Wajima, T., et al.: J. Med. Microbiol., 57, 1383 (2008)
• Isoherranen, N., et al.: Chem. Res. Toxicol., 22, 294 (2008)