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

• ChemBase ID: 104713
• Molecular Formular: C18H37N5O9
• Molecular Mass: 467.51448
• Monoisotopic Mass: 467.25912779
• SMILES: NCC1OC(OC2C(N)CC(N)C(OC3OC(CO)C(O)C(N)C3O)C2O)C(N)CC1O
• Canonical SMILES: NCC1OC(OC2C(N)CC(C(C2O)OC2OC(CO)C(C(C2O)N)O)N)C(CC1O)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
• InChIKey: NLVFBUXFDBBNBW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-2-[(4,6-diamino-3-{[3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-6-(hydroxymethyl)oxane-3,5-diol
• IUPAC Traditional name: tobramycin; @tobramycin
• 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 Deuterated; Nebramycin 6- Deuterated; Nebramycin VI- Deuterated; Tobramax-Deuterated; Tobramaxin- Deuterated; Tobrex-Deuterated; Tobramycin Deuterated; Distobram; Gernebcin; Nebramycin Factor 6; NF 6; Obramycin; Tobradistin; Tobrex; TOBRAMYCIN

Database IDs

• CAS Number: 32986-56-4
• EC Number: 251-322-5
• PubChem SID: 162093094
• PubChem CID: 5496

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: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 177-181°C

Safety Information

• Storage Condition: 2-8°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: WK2100000

DETAILS

Toronto Research Chemicals - T524002

Single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. Antibacterial.A representative lot contains d4, d5, d6, d7, d8, and d9.

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)