{[(2R,3R,4S,5R)-6-[(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: 132629
• Molecular Formular: C18H34ClN2O8PS
• Molecular Mass: 504.962921
• Monoisotopic Mass: 504.14620137
• SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)NC(C1[C@@H]([C@@H]([C@H]([C@H](O1)SC)OP(=O)(O)O)O)O)[C@H](C)Cl
• Canonical SMILES: CCC[C@H]1CN([C@@H](C1)C(=O)NC(C1O[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+/m0/s1
• InChIKey: UFUVLHLTWXBHGZ-MWBQRTRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5R)-6-[(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)-6-[(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: Clindamycin 2-dihydrogen phosphate; Clindamycin 2-phosphate

Database IDs

• CAS Number: 24729-96-2
• EC Number: 246-433-0
• MDL Number: MFCD07793328
• PubChem SID: 162226906; 24892866
• PubChem CID: 16219148

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

Safety Information

• RTECS: GF2625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Pharmacopeia Traceability: traceable to PhEur C2269000; traceable to USP 1138008
• Empirical Formula (Hill Notation): C18H34ClN2O8PS

DETAILS

Sigma Aldrich - C6427

Biochem/physiol Actions
Spectrum of Activity: Gram positive cocci and taxoplasma. Especially active against anaerobic bacteria.Mode of Action: Inhibits protein synthesis in bacterial by binding the 50s ribosomal subunit.
Clindamycin 2-phosphate is a pharmacological tyrosyl-DNA phosphodiesterase (Tdp1) inhibitor. Clindamycin 2-phosphate can repair DNA topoisomerase I-DNA covalent complexes by hydrolyzing the tyrosyl-DNA bond. It inhibits protein synthesis in bacteria by binding the 50s ribosomal subunit. 2. Spectrum of Activity: Gram positive cocci and taxoplasma. Especially active against anaerobic bacteria.
Other Notes
Antibacterial and antiprotozoal antibiotic of the licosamide class.
Application
Clindamycin 2-phosphate is an aminoglycoside antibiotic that has been used to study the cytoxicity of antibiotics on human cell lines 1, Bacterial protein synthesis and peptide translation, and the inhibition of human Tyrosyl-DNA Phosphodiesterase 2.

Sigma Aldrich - 80328

Biochem/physiol Actions
Spectrum of Activity: Gram positive cocci and taxoplasma. Especially active against anaerobic bacteria.Mode of Action: Inhibits protein synthesis in bacterial by binding the 50s ribosomal subunit.
Other Notes
Antibacterial and antiprotozoal antibiotic of the licosamide class.