(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-(2H3)methyl-4-propylpyrrolidine-2-carboxamide

• ChemBase ID: 172304
• Molecular Formular: C18H34N2O6S
• Molecular Mass: 406.53736
• Monoisotopic Mass: 406.21375782
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)O)O)O)([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)O)O)[C@@H](O)C)C
• InChI: InChI=1S/C18H34N2O6S/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)/t9?,10-,11+,12?,13+,14-,15-,16-,18-/m1/s1
• InChIKey: OJMMVQQUTAEWLP-NOWPCOIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-(^2H₃)methyl-4-propylpyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-(^2H₃)methyl-4-propylpyrrolidine-2-carboxamide
• Synonyms: (2S-trans)-Methyl 6,8-Dideoxy-6-[[(1-methyl-d3-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-α-D-galacto-octopyranoside; Lincocin-d3; Lincogap-d3; NSC 70731-d3; U 10149a-d3; Lincomycin-d3

Database IDs

• PubChem SID: 164228214
• PubChem CID: 71749788

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: Chloroform; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 63-66°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L466202

Labelled Lincomycin. 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

• 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)