(2R)-N-{2-hydroxy-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

• ChemBase ID: 168060
• Molecular Formular: C18H35ClN2O6S
• Molecular Mass: 442.9983
• Monoisotopic Mass: 442.19043553
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)SC)O)O)O)(C(O)C)NC(=O)[C@H]1CC(CN1C)CCC.Cl
• Canonical SMILES: CCCC1CN([C@H](C1)C(=O)NC(C1O[C@H](SC)C([C@H]([C@H]1O)O)O)C(O)C)C.Cl
• InChI: InChI=1S/C18H34N2O6S.ClH/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H/t9?,10?,11-,12?,13-,14-,15?,16?,18-;/m1./s1
• InChIKey: POUMFISTNHIPTI-KBTFJHITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-{2-hydroxy-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (2R)-N-{2-hydroxy-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• Synonyms: Methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1- thio-L-threo-α-D-galacto-octopyranoside Hydrochloride; trans-α-Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-D-galacto-octopyranoside Hydrochloride; (7S)-Lincomycin Hydrochloride; 7-Deoxy-7(S)-hydroxylincomycin Hydrochloride; Epilincomycin Hydrochloride; U 20244E Hydrochloride; 7-Epi Lincomycin Hydrochloride Salt; (2S-trans)-Methyl 6,8-Dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D3-threo-α-D-galactooctopyranoside Hydrochloride; Lincocin; Lincogap; NSC 70731; U 10149a; Lincomycin Hydrochloride

Database IDs

• CAS Number: 859-18-7
• PubChem SID: 162262192
• PubChem CID: 46782061

CALCULATED PROPERTIES

• Acid pKa: 12.365502
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.7498562
• LogD (pH = 7.4): -0.99001026
• Log P: -0.3168542
• Molar Refractivity: 102.6663 cm^3
• Polarizability: 41.491238 Å^3
• Polar Surface Area: 122.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Crystalline Solid; White Solid
• Melting Point: >159°C (dec.); 148-150°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator

DETAILS

Toronto Research Chemicals - 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 - 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. Antibacterial.

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)