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

• ChemBase ID: 172305
• Molecular Formular: C17H33ClN2O6S
• Molecular Mass: 428.97172
• Monoisotopic Mass: 428.17478547
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)SC)O)O)O)(C(O)C)NC(=O)[C@H]1CC(CN1C)CC.Cl
• Canonical SMILES: CCC1CN([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/C17H32N2O6S.ClH/c1-5-9-6-10(19(3)7-9)16(24)18-11(8(2)20)15-13(22)12(21)14(23)17(25-15)26-4;/h8-15,17,20-23H,5-7H2,1-4H3,(H,18,24);1H/t8?,9?,10-,11?,12-,13-,14?,15?,17-;/m1./s1
• InChIKey: MGUWHIXJDICIPX-OVKWTFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-4-ethyl-N-{2-hydroxy-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methylpyrrolidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (2R)-4-ethyl-N-{2-hydroxy-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methylpyrrolidine-2-carboxamide hydrochloride
• Synonyms: (2S-trans)-Methyl 6,8-Dideoxy-6-[[(4-ethyl-1-methyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-erythro-α-D-galactooctopyranoside MonoHydrochloride; trans-4'-Ethyllincomycin Hydrochloride; Lincomycin B Hydrochloride

Database IDs

• CAS Number: 11021-35-5
• PubChem SID: 164228215
• PubChem CID: 71749789

CALCULATED PROPERTIES

• Acid pKa: 12.355208
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.142518
• LogD (pH = 7.4): -1.3906288
• Log P: -0.7614229
• Molar Refractivity: 98.0653 cm^3
• Polarizability: 39.661934 Å^3
• Polar Surface Area: 122.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L466225

Lincomycin (L466200) analog.

REFERENCES

• Argoudelis, A.D., et al.: Biochemistry, 4, 698 (1965)
• Magerlein, B.J., et al.: Antimicrob. Agents Chemother., 1966, 727 (1965)