2-[(4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol

• ChemBase ID: 175080
• Molecular Formular: C21H41N5O7
• Molecular Mass: 475.57954
• Monoisotopic Mass: 475.30059868
• SMILES: C1C(C(OC(=C1)CN)OC1C(C(C(CC1N)NCC)OC1C(C(C(CO1)(C)O)NC)O)O)N
• Canonical SMILES: CCNC1CC(N)C(C(C1OC1OCC(C(C1O)NC)(C)O)O)OC1OC(=CCC1N)CN
• InChI: InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3
• InChIKey: CIDUJQMULVCIBT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: netilmicin
• Synonyms: O-3-Deoxy-4-C-methyl-3-(methylamino)-β-l-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1-4)]-2-deoxy-N’-ethyl-D-streptamine; Certomycin; Netililn; Netilyn; Netromicine; Netromycin; Nettacin; Vectacin; Netilmicin Sulfate

Database IDs

• CAS Number: 56391-57-2
• PubChem SID: 164230990
• PubChem CID: 4460

CALCULATED PROPERTIES

• Acid pKa: 12.548514
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -17.568405
• LogD (pH = 7.4): -11.058617
• Log P: -3.529179
• Molar Refractivity: 119.8439 cm^3
• Polarizability: 49.31896 Å^3
• Polar Surface Area: 199.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: >194°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N390800

Semisynthetic aminoglycoside antibiotic, related to sisomicin. Antibacterial.

REFERENCES

• Miller, G.H., et al.: Antimicrob. Agents Chemother., 10, 827 (1976)
• Raab, W., et al.: Adv. Clin. Pharmacol., 15, 91 (1976)
• Noone, P., et al.: Drugs, 27, 548 (1976)