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

• ChemBase ID: 169578
• Molecular Formular: C13H27N3O6
• Molecular Mass: 321.36998
• Monoisotopic Mass: 321.1899856
• SMILES: O[C@H]1[C@@H](C([C@@H](CC1N)N)O[C@@H]1[C@@H](C([C@](CO1)(O)C)NC)O)O
• Canonical SMILES: CNC1[C@@H](O)[C@H](OC[C@]1(C)O)OC1[C@H](N)CC([C@H]([C@@H]1O)O)N
• InChI: InChI=1S/C13H27N3O6/c1-13(20)4-21-12(9(19)11(13)16-2)22-10-6(15)3-5(14)7(17)8(10)18/h5-12,16-20H,3-4,14-15H2,1-2H3/t5?,6-,7-,8+,9-,10?,11?,12-,13+/m1/s1
• InChIKey: ONKJLIUSEXIAKL-VJGRRVINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2-{[(2S,3R,6R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: (2R,3R,5R)-2-{[(2S,3R,6R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• Synonyms: 2-Deoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-streptamine Triacetate; Garamine Triacetate Salt (Gentamicin Impurity)

Database IDs

• PubChem SID: 162263710
• PubChem CID: 71317041

CALCULATED PROPERTIES

• Acid pKa: 12.5102415
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -12.141459
• LogD (pH = 7.4): -8.299577
• Log P: -3.839704
• Molar Refractivity: 75.514 cm^3
• Polarizability: 31.786764 Å^3
• Polar Surface Area: 163.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G245300

Gentamicin (G360600) impurity.

REFERENCES

• Von Ahsen, U., et al.: J. Mol. Biol., 226, 935 (1992)
• Grahek, R., et al.: J. Pharm. Biomed. Anal., 50, 1037 (1992)