(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-6-(methylsulfanyl)-3,4,5-tris[(trimethylsilyl)oxy]oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

• ChemBase ID: 179254
• Molecular Formular: C27H58N2O6SSi3
• Molecular Mass: 623.08072
• Monoisotopic Mass: 622.33233818
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)([C@@H](O)C)NC(=O)[C@@H]1C[C@@H](CN1C)CCC
• Canonical SMILES: CCC[C@@H]1CN([C@@H](C1)C(=O)N[C@H]([C@H]1O[C@H](SC)[C@@H]([C@@H]([C@H]1O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C)C
• InChI: InChI=1S/C27H58N2O6SSi3/c1-14-15-19-16-20(29(3)17-19)26(31)28-21(18(2)30)22-23(33-37(5,6)7)24(34-38(8,9)10)25(27(32-22)36-4)35-39(11,12)13/h18-25,27,30H,14-17H2,1-13H3,(H,28,31)/t18?,19-,20+,21?,22-,23+,24+,25-,27-/m1/s1
• InChIKey: PKNYTEMTZAKTHT-CEFDCSDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-6-(methylsulfanyl)-3,4,5-tris[(trimethylsilyl)oxy]oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide; (2S,4R)-N-[(1R,2S)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-6-(methylsulfanyl)-3,4,5-tris[(trimethylsilyl)oxy]oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S,4R)-N-[(1R,2S)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-6-(methylsulfanyl)-3,4,5-tris[(trimethylsilyl)oxy]oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide; (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-6-(methylsulfanyl)-3,4,5-tris[(trimethylsilyl)oxy]oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• Synonyms: 2,3,4-Tri-O-trimethylsilylepilincomycin; Methyl 6,8-Dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-2,3,4-tris-O-(trimethylsilyl)-D-erythro-α-D-galacto-octopyranoside; 2,3,4-Tri-O-trimethylsilyllincomycin; Methyl 6,8-Dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-2,3,4-tris-O-(trimethylsilyl)-L-threo-α-D-galacto-octopyranoside

Database IDs

• CAS Number: 25420-97-7
• PubChem SID: 164235164
• PubChem CID: 71752839

CALCULATED PROPERTIES

• Acid pKa: 12.975599
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 3.156653
• LogD (pH = 7.4): 4.935982
• Log P: 5.6094
• Molar Refractivity: 151.044 cm^3
• Polarizability: 67.029915 Å^3
• Polar Surface Area: 89.49 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T796865

Protected 7-Epi lincomycin (E588550). An epimer of Lincomycin (L466200); a 6-amino, 6-deoxy-octopyraninose with strong antibiotic activity. A less potent bactericidal than its (7R)-epimer.

Toronto Research Chemicals - T796860

Protected Lincomycin (L466200). An antibiotic produced by Streptomyces lincolnensis. Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA. Inhibits bacterial protein synthesis. Antibacte

REFERENCES

• Le Goffic, F. et al.: J. Antimicrob. Chemother., 16, 12 (1985)
• Prior, C. et al.: J. Pharmacol. Exp. Therap., 255, 1170 (1985)
• Mason, D.J., et al.: Antimicrob. Agents Chemother., 555 (1962)
• Gray, et al.: Toxicol. Appl. Pharmacol., 6, 476 (1962)
• Muti, H.Y., et al.: Anal. Profiles Drug Subs. Excip., 23, 269 (1962)