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

• ChemBase ID: 164845
• Molecular Formular: C18H34ClN2O8PS
• Molecular Mass: 504.962921
• Monoisotopic Mass: 504.14620137
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)O)O)OP(=O)(O)O)([C@H](Cl)C)NC(=O)[C@@H]1C[C@@H](CN1C)CCC
• 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]1OP(=O)(O)O)O)O)[C@H](Cl)C)C
• InChI: InChI=1S/C18H34ClN2O8PS/c1-5-6-10-7-11(21(3)8-10)17(24)20-12(9(2)19)15-16(29-30(25,26)27)13(22)14(23)18(28-15)31-4/h9-16,18,22-23H,5-8H2,1-4H3,(H,20,24)(H2,25,26,27)/t9?,10-,11+,12?,13-,14-,15-,16-,18-/m1/s1
• InChIKey: OZDNESASKLVYBG-PPAJBYOBSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 54887-30-8
• PubChem SID: 162258979
• PubChem CID: 71314906

CALCULATED PROPERTIES

• Acid pKa: 0.9302739
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.6952036
• LogD (pH = 7.4): -2.164776
• Log P: -0.5677443
• Molar Refractivity: 116.5902 cm^3
• Polarizability: 47.154106 Å^3
• Polar Surface Area: 148.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C580020

Clindamycin (C580000) impurity.

REFERENCES

• Coats, J.H., et al.: J. Bacteriology, 108, 459 (1971)
• Brown, L.W., et al.: J. Pharma. Sci., 67, 1254 (1971)