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

• ChemBase ID: 164846
• Molecular Formular: C17H31ClN2O5S
• Molecular Mass: 410.95644
• Monoisotopic Mass: 410.16422078
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)SC)O)O)O)(C(Cl)C)NC(=O)[C@H]1CC(CN1C)CC
• Canonical SMILES: CCC1CN([C@H](C1)C(=O)NC(C1O[C@H](SC)C([C@H]([C@H]1O)O)O)C(Cl)C)C
• InChI: InChI=1S/C17H31ClN2O5S/c1-5-9-6-10(20(3)7-9)16(24)19-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-4/h8-15,17,21-23H,5-7H2,1-4H3,(H,19,24)/t8?,9?,10-,11?,12-,13-,14?,15?,17-/m1/s1
• InChIKey: UHQYIIRIOVIPLI-QBFRQILCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-4-ethyl-1-methylpyrrolidine-2-carboxamide
• IUPAC Traditional name: (2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-4-ethyl-1-methylpyrrolidine-2-carboxamide
• Synonyms: Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-1-methyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside; (2S-trans)-Methyl 7-Chloro-6,7,8-trideoxy-6-[[(4-ethyl-1-methyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside; Clindamycin B

Database IDs

• CAS Number: 18323-43-8
• PubChem SID: 162258980
• PubChem CID: 71314907

CALCULATED PROPERTIES

• Acid pKa: 12.138641
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.3724707
• LogD (pH = 7.4): 0.2538384
• Log P: 0.593169
• Molar Refractivity: 101.1163 cm^3
• Polarizability: 40.877544 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 77-84°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C580040

A minor impuritiy of Clindamycin (C580000) in bulk drug.

REFERENCES

• Duckworth, C., et al.: J. Antimicrob. Agents Chemother., 31, 581(1993)
• Orwa, J., et al.: J. Pharm. Biomed. Anal., 23, 771 (1993)
• Platzer, D., et al.: J. Pharm. Biomed. Anal., 41, 84 (1993)