(2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-methanesulfinyloxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

• ChemBase ID: 164843
• Molecular Formular: C18H34Cl2N2O6S
• Molecular Mass: 477.44336
• Monoisotopic Mass: 476.15146318
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)S(=O)C)O)O)O)(C(Cl)C)NC(=O)[C@H]1CC(CN1C)CCC.Cl
• Canonical SMILES: CCCC1CN([C@H](C1)C(=O)NC(C1O[C@H](S(=O)C)C([C@H]([C@H]1O)O)O)C(Cl)C)C.Cl
• InChI: InChI=1S/C18H33ClN2O6S.ClH/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(27-16)28(4)26;/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25);1H/t9?,10?,11-,12?,13-,14-,15?,16?,18-,28?;/m1./s1
• InChIKey: BDSYDLWSVWOCSU-UEHJQROMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-methanesulfinyloxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-methanesulfinyloxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• Synonyms: 7-Chloro-1,6,7,8-tetradeoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-(methylsulfinyl)-L-threo-α-D-galactooctopyranose; 7(S)-Chloro-7-deoxylincomycin Sulfoxide; U 25026A; Clindamycin Sulfoxide

Database IDs

• CAS Number: 22431-46-5
• PubChem SID: 162258977
• PubChem CID: 46781044

CALCULATED PROPERTIES

• Acid pKa: 11.993099
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.3457212
• LogD (pH = 7.4): -1.0862275
• Log P: -0.97799516
• Molar Refractivity: 107.32 cm^3
• Polarizability: 43.304043 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 85-88°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C580010

A Clindamycin metabolite.

REFERENCES

• Li, L., et al.: J. Antibiotics, 30, 506 (1977)
• Wynalda, M., et al.: Drug Metab. Disposition, 31, 878 (1977)