(2S,4S,5S)-4-amino-2-{[(3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol

• ChemBase ID: 178685
• Molecular Formular: C18H37N5O9
• Molecular Mass: 467.51448
• Monoisotopic Mass: 467.25912779
• SMILES: [C@@H]1(OC([C@H](CC1N)O)CN)O[C@H]1C(C([C@@H](CC1N)N)O[C@H]1OC([C@H]([C@@H](C1O)N)O)CO)O
• Canonical SMILES: NCC1O[C@H](O[C@@H]2C(N)C[C@H](C(C2O)O[C@H]2OC(CO)[C@H]([C@@H](C2O)N)O)N)C(C[C@@H]1O)N
• InChI: InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5?,6-,7?,8+,9?,10?,11+,12-,13?,14?,15-,16?,17-,18-/m1/s1
• InChIKey: NLVFBUXFDBBNBW-SNKXVCFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-4-amino-2-{[(3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
• IUPAC Traditional name: (2S,4S,5S)-4-amino-2-{[(3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
• Synonyms: O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1-6)-O-[2,6-diamino-2,3,6-trideoxy-α -D-ribo-hexopyranosyl-(1-4)]-2-deoxy-D-streptamine; Nebramycin 6; Nebramycin VI; Tobramax; Tobramaxin; Tobrex; Tobramycin

Database IDs

• CAS Number: 32986-56-4
• PubChem SID: 164234595
• PubChem CID: 71752596

CALCULATED PROPERTIES

• Acid pKa: 12.542545
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -20.344318
• LogD (pH = 7.4): -13.627587
• Log P: -6.4775004
• Molar Refractivity: 106.6949 cm^3
• Polarizability: 45.42405 Å^3
• Polar Surface Area: 268.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 215-218°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T524000

Single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. Antibacterial.

REFERENCES

• Koch, K.F., et al.: Antimicrob. Agents Chemother., 309 (1970)
• Welles, J.S., et al.: Toxicol. Appl. Pharmacol., 22, 332 (1970)
• Dash, A.K., et al.: Anal. Profiles Drug Subs. Excip., 24, 579 (1970)