4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid sodium

• ChemBase ID: 133661
• Molecular Formular: C15H16Cl2N2NaO8
• Molecular Mass: 446.19191
• Monoisotopic Mass: 445.01814012
• SMILES: c1cc(ccc1[C@H]([C@@H](COC(=O)CCC(=O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-].[Na]
• Canonical SMILES: OC(=O)CCC(=O)OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl.[Na]
• InChI: InChI=1S/C15H16Cl2N2O8.Na/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26;/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21);/t10-,13-;/m1./s1
• InChIKey: OQAWGHRXAVKAIG-HTMVYDOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid sodium
• IUPAC Traditional name: chloramphenicol succinate sodium
• Synonyms: Chloramphenicol α-succinate; Chloramphenicol succinate sodium salt

Database IDs

• CAS Number: 982-57-0
• EC Number: 213-568-1
• MDL Number: MFCD00079025
• PubChem SID: 162227938; 24892643
• PubChem CID: 16219114

CALCULATED PROPERTIES

• Acid pKa: 3.6750705
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.6805518
• LogD (pH = 7.4): -2.3224185
• Log P: 1.1446916
• Molar Refractivity: 93.2455 cm^3
• Polarizability: 36.007523 Å^3
• Polar Surface Area: 158.75 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: AB6905000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: ≥80% (HPLC)

DETAILS

Sigma Aldrich - C3787

Application
Chloramphenicol is used as a selection agent for transformed cells containing a chloramphenicol resistance gene and is used to halt protein synthesis 1.
Biochem/physiol Actions
Chloramphenicol inhibits bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit. Used as a selection agent for transformed cells containing a chloramphenicol resistance gene.
Chloramphenicol inhibits bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit.