G 418 sulfate (Geneticin sulfate), Aminoglycoside antibiotic agent

Key facts

CAS number

49662-05-7

Form

Solid

form

Source

Micromonospora rhodorangea

Molecular weight

692.7 Da

Molecular formula

C₂₀H₄₄N₄O₁₈S₂

PubChem

206347

Nature

Native

Solubility

Soluble in water to 100 mM

Biochemical name

G-418 sulfate

Biological description

Aminoglycoside antibiotic agent. Potent Delta7-SMN target sequence inducer. Inhibits amino acid incorporation into proteins. Shows cytotoxic effects. Inhibits the prokaryotic and eukaryotic elongation cycle. Shows antibacterial and antiprotozoal effects in vivo.

Canonical smiles

CC(C1C(C(C(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)O)O)O.OS(=O)(=O)O.OS(=O)(=O)O

Isomeric smiles

C[C@H]([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)O)O)O.OS(=O)(=O)O.OS(=O)(=O)O

InChi

InChI=1S/C20H40N4O10.2H2O4S/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19;2*1-5(2,3)4/h6-19,24-30H,4-5,21-23H2,1-3H3;2*(H2,1,2,3,4)/t6-,7+,8-,9-,10-,11+,12+,13-,14-,15-,16+,17-,18-,19-,20+;;/m1../s1

InChiKey

UHEPSJJJMTWUCP-DHDYTCSHSA-N

IUPAC Name

(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-[(1R)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;sulfuric acid