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

• ChemBase ID: 175037
• Molecular Formular: C12H26N4O6
• Molecular Mass: 322.35804
• Monoisotopic Mass: 322.18523457
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CN)O[C@H]1[C@@H](C([C@@H](CC1N)N)O)O)N)O)O
• Canonical SMILES: NCC1O[C@H](O[C@@H]2C(N)C[C@H](C([C@H]2O)O)N)C([C@H]([C@@H]1O)O)N
• InChI: InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4?,5?,6?,7?,8-,9-,10-,11-,12-/m1/s1
• InChIKey: SYJXFKPQNSDJLI-HYEKRMOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,4R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}oxane-3,4-diol
• IUPAC Traditional name: (3S,4R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,4R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}oxane-3,4-diol
• Synonyms: 2-Deoxy-4-O-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl)-D-streptamine Hydrochloride; Neomycin A Tetrahydrochloride; Neamine Hydrochloride

Database IDs

• CAS Number: 15446-43-2
• PubChem SID: 164230947
• PubChem CID: 68321693

CALCULATED PROPERTIES

• Acid pKa: 12.657486
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -15.799769
• LogD (pH = 7.4): -10.133399
• Log P: -5.2900777
• Molar Refractivity: 73.7212 cm^3
• Polarizability: 31.491682 Å^3
• Polar Surface Area: 203.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N386000

Neamine is normally found as a core structure of aminoglycoside antibiotics. It is used in the synthesis of disaccharide neamine derivatives as antibacterial agents.

REFERENCES

• Kawaguchi, H., et al.: J. Antibiot., 25, 695 (1972)
• Fourmy, D., et al.: Science, 274, 1367 (1972)
• Riguet, E., et al.: J. Med. Chem., 47, 4806 (2004)