(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-ethyl-1-(2H3)methylpyrrolidine-2-carboxamide

• ChemBase ID: 164847
• Molecular Formular: C17H31ClN2O5S
• Molecular Mass: 410.95644
• Monoisotopic Mass: 410.16422078
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)O)O)O)([C@H](Cl)C)NC(=O)[C@@H]1C[C@@H](CN1C)CC
• Canonical SMILES: CC[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](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-KSOBAXNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-ethyl-1-(^2H₃)methylpyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-ethyl-1-(^2H₃)methylpyrrolidine-2-carboxamide
• Synonyms: Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-1-(methyl-d3)-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-d3)-2-pyrrolidinyl)carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside; Clindamycin B-d3

Database IDs

• PubChem SID: 162258981
• PubChem CID: 71314908

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

DETAILS

Toronto Research Chemicals - C580042

A minor labelled 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)