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

• ChemBase ID: 164841
• Molecular Formular: C18H34Cl2N2O5S
• Molecular Mass: 461.44396
• Monoisotopic Mass: 460.15654856
• 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)CCC.Cl
• Canonical SMILES: CCC[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.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-GQYOKNPUSA-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]-1-(^2H₃)methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• 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]-1-(^2H₃)methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• Synonyms: (2S-trans)-Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-(methyl-d3)-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside Hydrochloride; 7(S)-Chloro-7-deoxylincomycin-d3; 7-CDL-d3; 7-Chlorolincomycin-d3; Antirobe-d3; Chlolincocin-d3; Cleocin-d3; Clinimycin-d3; Dalacine-d3; Clindamycin-d3 Hydrochloride

Database IDs

• PubChem SID: 162258975
• PubChem CID: 71314902

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: Water
• Apperance: White Solid
• Melting Point: 148-150°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C580002

Labelled Clindamycin. Semi-synthetic antibiotic prepared from Lincomycin. Antibacterial.

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)