(2S)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propyl-2,5-dihydro-1H-pyrrole-2-carboxamide

• ChemBase ID: 165379
• Molecular Formular: C18H31ClN2O5S
• Molecular Mass: 422.96714
• Monoisotopic Mass: 422.16422078
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)SC)O)O)O)(C(Cl)C)NC(=O)[C@@H]1C=C(CN1C)CCC
• Canonical SMILES: CCCC1=C[C@H](N(C1)C)C(=O)NC(C1O[C@H](SC)C([C@H]([C@H]1O)O)O)C(Cl)C
• InChI: InChI=1S/C18H31ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h7,9,11-16,18,22-24H,5-6,8H2,1-4H3,(H,20,25)/t9?,11-,12?,13+,14+,15?,16?,18+/m0/s1
• InChIKey: RMQIGGGBJDZABU-NKSLOEKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propyl-2,5-dihydro-1H-pyrrole-2-carboxamide
• IUPAC Traditional name: (2S)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propyl-2,5-dihydropyrrole-2-carboxamide
• Synonyms: Methyl (7R)-Chloro-6,7,8-trideoxy-6-[[[(2S)-2,3-dihydro-1-methyl-4-propyl-1H-pyrrol-2-yl]carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside; Dehydro 7-Epi ClindamycinDISCONTINUED

Database IDs

• PubChem SID: 162259512
• PubChem CID: 71315173

CALCULATED PROPERTIES

• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 12.094042
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.3474073
• LogD (pH = 7.4): 0.78895444
• Log P: 0.86601937
• Molar Refractivity: 106.3363 cm^3
• Polarizability: 42.457203 Å^3

DETAILS

Toronto Research Chemicals - D229595

An epimeric impurity of the semi-synthetic antibiotic drug Clindamycin (C580000).

REFERENCES

• Zhou, H., et al.: J. Pharma. Biomed. Anal., 41, 1116 (2006)
• Birkenmeyer, R.D., et al.: J. Med. Chem., 13, 616 (2006)