2-[(4,6-diamino-3-{[3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol

• ChemBase ID: 169615
• Molecular Formular: C20H41N5O7
• Molecular Mass: 463.56884
• Monoisotopic Mass: 463.30059868
• SMILES: C1CC(C(OC1C(N)C)OC1C(C(C(CC1N)N)OC1C(C(C(CO1)(O)C)NC)O)O)N
• Canonical SMILES: CNC1C(O)C(OCC1(C)O)OC1C(N)CC(C(C1O)OC1OC(CCC1N)C(N)C)N
• InChI: InChI=1S/C20H41N5O7/c1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19/h8-19,25-28H,4-7,21-24H2,1-3H3
• InChIKey: XUFIWSHGXVLULG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4,6-diamino-3-{[3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: 2-[(4,6-diamino-3-{[3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• Synonyms: O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(16)-O-[2,6-diamino-2,3,4,6,7-pentadeoxy-α-D-ribo-heptopyranosyl-(14)]-2-deoxy-D-streptamine Pentaacetate Salt; Gentamicin C2 Pentaacetate Salt

Database IDs

• CAS Number: 25876-11-3
• PubChem SID: 162263747
• PubChem CID: 588785

CALCULATED PROPERTIES

• Acid pKa: 12.548904
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -17.909746
• LogD (pH = 7.4): -12.029432
• Log P: -3.569736
• Molar Refractivity: 113.2461 cm^3
• Polarizability: 47.735172 Å^3
• Polar Surface Area: 213.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Light Beige Solid
• Melting Point: 84-89°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G360595

Antibacterial. A mixture of Gentamicin C2 and Gentamycin C2a.

REFERENCES

• Holt, H.A., et al.: J. Antimicrob. Chemother., 34, 747 (1994)
• Wilschanski, M., et al.: Am. J. Respir. Crit. Care Med., 161, 860 (1994)