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

• ChemBase ID: 164842
• 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)OP(=O)(O)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]1O)O)OP(=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)15-13(22)14(23)16(18(28-15)31-4)29-30(25,26)27/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: UFUVLHLTWXBHGZ-KUWMELJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5R,6R)-6-[(1S,2S)-2-chloro-1-{[(2S,4R)-1-methyl-4-propylpyrrolidin-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)-1-methyl-4-propylpyrrolidin-2-yl]formamido}propyl]-4,5-dihydroxy-2-(methylsulfanyl)oxan-3-yl]oxyphosphonic acid
• Synonyms: Methyl 7-Chloro-6,7,8-trideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidine-carboxamido)-1-thio-L-threo-α-D-galactooctopyranoside 2-(Dihydrogen Phosphate); 7(S)-Chloro-7-deoxylincomycin 2-Phosphate; Cleocin T; Cleocin Phosphate; Clinadac; Clindagel; Clindesse; Clindets; Dalacin P; Dalacin T; NSC 618653; Clindamycin 2-Phosphate

Database IDs

• CAS Number: 24729-96-2
• PubChem SID: 162258976
• PubChem CID: 71314904

CALCULATED PROPERTIES

• Acid pKa: 0.7088429
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.7629697
• LogD (pH = 7.4): -2.3505592
• Log P: -0.5666045
• Molar Refractivity: 116.5902 cm^3
• Polarizability: 47.154118 Å^3
• Polar Surface Area: 148.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 187-192°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C580005

A highly water soluble Clindamycin prodrug.

REFERENCES

• Ozensoy, O., et al.: J. Enz. Inhibit. Med. Chem., 23, 579 (2008)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2008)
• Dubina, M., et al.: Arch. Dermatol., 145, 1027 (2008)