(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol; bis(sulfuric acid)

• ChemBase ID: 132843
• Molecular Formular: C18H40N4O19S2
• Molecular Mass: 680.6556
• Monoisotopic Mass: 680.17281708
• SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)N.OS(=O)(=O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OS(=O)(=O)O.OC[C@H]1O[C@H](O[C@H]2[C@H](N)C[C@@H]([C@H]([C@@H]2O)O[C@H]2O[C@H](CN)[C@H]([C@@H]([C@H]2O)O)O)N)[C@@H]([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C18H36N4O11.2H2O4S/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17;2*1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;2*(H2,1,2,3,4)/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;;/m1../s1
• InChIKey: OGTKIXVMLDAMNU-KNQICTBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol; bis(sulfuric acid)
• IUPAC Traditional name: kanamycin; bis(sulfuric acid)
• Synonyms: Kanamycin A; Kanamycin disulfate salt from Streptomyces kanamyceticus; Kanamycin 硫酸氢盐; Kanamycin 二硫酸盐 来源于卡那霉素链霉菌

Database IDs

• CAS Number: 64013-70-3
• MDL Number: MFCD00143916
• PubChem SID: 162227120
• PubChem CID: 24721551

CALCULATED PROPERTIES

• Acid pKa: 12.109839
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -18.059649
• LogD (pH = 7.4): -12.666778
• Log P: -7.0609136
• Molar Refractivity: 106.1345 cm^3
• Polarizability: 45.27121 Å^3
• Polar Surface Area: 282.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Potency: ~650 μg per mg
• Impurities: ≤4% Kanamycin B

DETAILS

Sigma Aldrich - K1876

Preparation Note
Kanamycin acid sulfate is prepared by solubilizing kanamycin sulfate in dilute sulfuric acid and drying. The sulfate content is approximately 25%.
Application
Aminoglycoside-antibiotic with broad antibacterial spectrum, (including mycobacteria, many gram-positive and most gram-negative organisms); Additive in culture media for the isolation of group D Streptococci on Kanamycin Esculin Azide Agar (Mossel et al.) or for selection of transformed plant cells containing the neomycin phosphotransferase (for kanamycin resistance); on a kanamycin-medium1,2. Kanamycin has been used for electrophysiological recordings of outer hair cells and inner hair cells3. It is used to inhibit shoot regeneration from Siberian Elmleaf explants4.
Biochem/physiol Actions
Kanamycin inhibits shoot regeneration of Siberian Elm leaf explants4. Kanamycin is an aminoglycoside antibiotic. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasm.