(2S,4S,5S)-4-amino-2-{[(1S,4S,6R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol

• ChemBase ID: 166015
• Molecular Formular: C12H25N3O7
• Molecular Mass: 323.3428
• Monoisotopic Mass: 323.16925016
• SMILES: [C@@H]1([C@@H](C[C@@H](C(C1O)O)N)N)O[C@H]1OC([C@H]([C@@H](C1O)N)O)CO
• Canonical SMILES: OCC1O[C@H](O[C@H]2[C@H](N)C[C@@H](C(C2O)O)N)C([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-9(19)6(15)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5?,6-,7?,8+,9?,10?,11-,12+/m0/s1
• InChIKey: WPYNTQYMFOTKRF-OYMVJXOKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-4-amino-2-{[(1S,4S,6R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
• IUPAC Traditional name: (2S,4S,5S)-4-amino-2-{[(1S,4S,6R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
• Synonyms: 6-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine; 4-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-L-Streptamine; Antibiotic NK 1012-2; Tobramycin A; Deoxystreptamine-kanosaminide

Database IDs

• CAS Number: 20744-51-8
• PubChem SID: 162260148
• PubChem CID: 71315512

CALCULATED PROPERTIES

• Acid pKa: 12.501202
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -13.215497
• LogD (pH = 7.4): -9.243694
• Log P: -5.183196
• Molar Refractivity: 72.0637 cm^3
• Polarizability: 30.648256 Å^3
• Polar Surface Area: 197.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: >135°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D263510

An impurity of Tobramycin (T524000).

REFERENCES

• Brandl, M. et al.: Drug Dev. Ind. Pharm., 18, 1423 (1992)
• Murase, M. et al.: Prog. Antimicrob. Anticancer Chemother., Proc. Int. Congr. Chemother., 6, 1098 (1992)