Chloramphenicol β-D-galactoside

Key facts

CAS number

191476-32-1

Form

Solid

form

Molecular weight

485.3 Da

Molecular formula

C₁₇H₂₂Cl₂N₂O₁₀

PubChem

53230086

Nature

Synthetic

Solubility

Soluble in DMSO

Soluble in water

Biochemical name

Chloramphenicol 1-O-b-D-galactopyranoside

Biological description

Chloramphenicol precursor that releases chloramphenicol upon enzymatic or chemical hydrolysis. Galactose is linked to the site of action of chloramphenicol via a hydrolysable bond.

Canonical smiles

C1=CC(=CC=C1C(C(COC2C(C(C(C(O2)CO)O)O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

Isomeric smiles

C1=CC(=CC=C1[C@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

InChi

InChI=1S/C17H22Cl2N2O10/c18-15(19)16(27)20-9(11(23)7-1-3-8(4-2-7)21(28)29)6-30-17-14(26)13(25)12(24)10(5-22)31-17/h1-4,9-15,17,22-26H,5-6H2,(H,20,27)/t9-,10-,11-,12+,13+,14-,17-/m1/s1

InChiKey

APNJPGQQUGNBMU-PRZACTIQSA-N

IUPAC Name

2,2-dichloro-N-[(1R,2R)-1-hydroxy-1-(4-nitrophenyl)-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]acetamide