{[(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-{[(2S,4R)-4-ethyl-1-methylpyrrolidin-2-yl]formamido}propyl]-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl]oxy}phosphonic acid

• ChemBase ID: 164848
• Molecular Formular: C17H32ClN2O8PS
• Molecular Mass: 490.936341
• Monoisotopic Mass: 490.1305513
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)OP(=O)(O)O)O)O)([C@H](Cl)C)NC(=O)[C@@H]1C[C@@H](CN1C)CC
• Canonical SMILES: CS[C@H]1O[C@H]([C@H]([C@H](Cl)C)NC(=O)[C@@H]2C[C@@H](CN2C)CC)[C@@H]([C@H]([C@H]1OP(=O)(O)O)O)O
• InChI: InChI=1S/C17H32ClN2O8PS/c1-5-9-6-10(20(3)7-9)16(23)19-11(8(2)18)14-12(21)13(22)15(17(27-14)30-4)28-29(24,25)26/h8-15,17,21-22H,5-7H2,1-4H3,(H,19,23)(H2,24,25,26)/t8?,9-,10+,11?,12-,13+,14-,15-,17-/m1/s1
• InChIKey: GOTDPKVMVWZIIW-FYZMILDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-{[(2S,4R)-4-ethyl-1-methylpyrrolidin-2-yl]formamido}propyl]-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-{[(2S,4R)-4-ethyl-1-methylpyrrolidin-2-yl]formamido}propyl]-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl]oxyphosphonic acid
• Synonyms: Methyl 7-Chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-1-methyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside 2-(Dihydrogen Phosphate) Monoammonium Salt; (2S-trans)-Methyl-7-Chloro-6,7,8-trideoxy-6-[[(4-ethyl-1-methyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-L-threo-α-D-galactooctopyranoside 2-(Dihydrogen Phosphate) Monoammonium Salt; Clindamycin B 2-Phosphate Ammonium Salt

Database IDs

• CAS Number: 54887-31-9
• PubChem SID: 162258982
• PubChem CID: 71314909

CALCULATED PROPERTIES

• Acid pKa: 0.70884335
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.2081946
• LogD (pH = 7.4): -2.822214
• Log P: -1.0111749
• Molar Refractivity: 111.9892 cm^3
• Polarizability: 45.3378 Å^3
• Polar Surface Area: 148.79 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C580050

The principal degradation product of Clindamycin 2-phosphate (C580005) in bulk drug and formulations.

REFERENCES

• Oesterling, T., et al.: J. Pharm. Sci., 59, 175 (1970)
• Munson, J., et al.: J. Pharm. Biomed. Anal., 3, 523 (1970)