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

Base Information

• Chemical Name: (3R,4R,5R)-2-[(2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(1-hydroxyethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• CAS No.: 49863-47-0
• Molecular Formula: C₂₀H₄₀N₄O₁₀
• Molecular Weight: 496.558
• Mol file: 49863-47-0.mol

Synonyms:antibiotic G 418;antibiotic G-418;G 418 sulfate;G-418;G418;Geneticin

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

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.1E-26mmHg at 25°C
• Melting Point: >193°C (dec.)
• Refractive Index: 1.625
• Boiling Point: 760.3 °C at 760 mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 413.6 °C
• PSA: 248.39000
• Density: 1.47 g/cm³
• LogP: -3.12120
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• XLogP3: -5.8
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 496.27444349
• Heavy Atom Count: 34
• Complexity: 681

Purity/Quality:

99%, ^*data from raw suppliers

G418 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Isomeric SMILES: CC([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H](C[C@@H](C([C@@H]2O)OC3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)O)O)O
• General Description: G418 (also known as Geneticin or Antibiotic G 418) is an aminoglycoside antibiotic with notable ototoxicity, making it one of the most toxic in its class. Research suggests that chemical modifications can mitigate its harmful effects on auditory cells while preserving its antibacterial efficacy, offering a potential pathway for developing safer aminoglycoside derivatives.

Refernces

Chemical Modifications Reduce Auditory Cell Damage Induced by Aminoglycoside Antibiotics

10.1021/jacs.9b12420

This study investigated auditory cell damage induced by aminoglycoside antibiotics, aiming to reduce their ototoxicity through chemical modifications while maintaining their antibacterial efficacy. The research team focused on apramycin (APR) and geneticin (G-418), two aminoglycosides considered to be among the least and most toxic, respectively. Using molecular dynamics simulations and experiments, the researchers discovered that chemical modifications could significantly impact the influence of these antibiotics on the essential movement freedom of the ribosome's decoding site, which in turn affects their ototoxicity. The results indicated that certain chemical modifications could reduce the auditory cell damage caused by aminoglycosides without affecting their antibacterial activity, suggesting a new paradigm for the development of safer aminoglycoside antibiotics. The chemicals used in the process included APR and G-418 and their semi-synthetic derivatives, as well as various molecules and compounds employed in the simulations and testing.

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