(3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}cyclohexane-1,2-diol

• ChemBase ID: 175049
• Molecular Formular: C12H26N4O5
• Molecular Mass: 306.35864
• Monoisotopic Mass: 306.19031995
• SMILES: [C@@H]1(OC([C@H](CC1N)O)CN)O[C@H]1C(C([C@@H](CC1N)N)O)O
• Canonical SMILES: NCC1O[C@H](O[C@@H]2C(N)C[C@H](C(C2O)O)N)C(C[C@@H]1O)N
• InChI: InChI=1S/C12H26N4O5/c13-3-8-7(17)2-6(16)12(20-8)21-11-5(15)1-4(14)9(18)10(11)19/h4-12,17-19H,1-3,13-16H2/t4-,5?,6?,7+,8?,9?,10?,11-,12-/m1/s1
• InChIKey: QBWLTQZEVUXXSR-PZLNIEEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}cyclohexane-1,2-diol
• IUPAC Traditional name: (3R,6R)-4,6-diamino-3-{[(2R,5S)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}cyclohexane-1,2-diol
• Synonyms: 2-Deoxy-4-O-(2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl)-D-streptamine Disulfate; 3'-Deoxyneamin Disulfate; 3'-Deoxyneamine Disulfate; 3'-Deoxyneomycin A Disulfate; Nebramycin VIII Disulfate; Tobramine Disulfate; Nebramine Disulfate

Database IDs

• CAS Number: 71122-29-7
• PubChem SID: 164230959
• PubChem CID: 71750972

CALCULATED PROPERTIES

• Log P: -4.599783
• Molar Refractivity: 72.6241 cm^3
• Polarizability: 30.817366 Å^3
• Polar Surface Area: 183.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false
• Acid pKa: 12.952368
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -15.494419
• LogD (pH = 7.4): -10.188987

DETAILS

Toronto Research Chemicals - N388250

A degradation product on the antibiotic Tobramycin (T524000).

REFERENCES

• Brandl, M. et al.: Drug Dev. Indust. Pharm., 18, 1423 (1992)
• Ghinami, C. et al.: J. Chrom. A, 1139, 52 (1992)