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

• ChemBase ID: 164840
• Molecular Formular: C18H34Cl2N2O5S
• Molecular Mass: 461.44396
• Monoisotopic Mass: 460.15654856
• SMILES: C(C1[C@@H]([C@@H](C([C@H](O1)SC)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](SC)C([C@H]([C@H]1O)O)O)C(Cl)C)C.Cl
• InChI: InChI=1S/C18H33ClN2O5S.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(26-16)27-4;/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25);1H/t9?,10?,11-,12?,13-,14-,15?,16?,18-;/m1./s1
• InChIKey: AUODDLQVRAJAJM-KBTFJHITSA-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}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (2R)-N-{2-chloro-1-[(3R,4R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• Synonyms: 7-Epi Clindamycin Hydrochloride; Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-α-D-galactooctopyranoside Hydrochloride; (2S-trans)-Methyl 7-Chloro-6,7,8-trideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-erythro-α-D-galactooctopyranoside Hydrochloride; Antibiotic U 21251F Hydrochloride; (2S-trans)-Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside Hydrochloride; 7(S)-Chloro-7-deoxylincomycin; 7-CDL; 7-Chloro-7-deoxylincomycin; 7-Chlorolincomycin; Antirobe; Chlolincocin; Cleocin; Clinimycin; Dalacine; Clindamycin Hydrochloride

Database IDs

• CAS Number: 21462-39-5
• PubChem SID: 162258974
• PubChem CID: 46781040

CALCULATED PROPERTIES

• Acid pKa: 12.163722
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.0028338
• LogD (pH = 7.4): 0.65432453
• Log P: 1.0377376
• Molar Refractivity: 105.7173 cm^3
• Polarizability: 42.705715 Å^3
• Polar Surface Area: 102.26 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Dark Yellow Solid; White Solid
• Melting Point: 141-147°C (dec.); 145-147°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - C580000

Semi-synthetic antibiotic prepared from Lincomycin. Antibacterial.

Toronto Research Chemicals - E582490

Clindamycin (C580000) impurity in bulk drug.

REFERENCES

• Birkenmeyer, R.D., et al.: J. Med. Chem., 13, 616 (1970)
• Oesterling, et al.: J. Pharm. Sci., 59, 63 (1970)
• Gray, J.E., et al.: Toxicol. Appl. Pharmacol., 21, 516 (1970)
• Brown, L.W., et al.: Anal. Profiles Drug Subs., 10, 75 (1970)
• Birkenmeyer, R., et al.: J. Med. Chem., 13, 616 (1970)
• Platzer, D., et al.: J. Pharm. Biomed. Anal., 41, 84 (1970)
• Platzer, D., et al.: J. Pharm. Biomed. Anal., 41, 84 (1970)