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

• ChemBase ID: 155122
• Molecular Formular: C18H39N5O14S
• Molecular Mass: 581.59236
• Monoisotopic Mass: 581.22142195
• 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)CO)O)N)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)N)N.OS(=O)(=O)O
• Canonical SMILES: 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]2N)O)O)N)[C@@H]([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C18H37N5O10.H2O4S/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18;1-5(2,3)4/h4-18,24-29H,1-3,19-23H2;(H2,1,2,3,4)/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+;/m0./s1
• InChIKey: YGTPKDKJVZOVCO-KELBJJLKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol; sulfuric acid
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol; sulfuric acid
• Synonyms: Bekanamycin sulfate salt; Kanamycin B sulfate salt

Database IDs

• MDL Number: MFCD00078511
• Beilstein Number: 5235274
• PubChem SID: 162249260; 24881934; 24891829
• PubChem CID: 636396

CALCULATED PROPERTIES

• Acid pKa: 12.488072
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -20.649662
• LogD (pH = 7.4): -13.571994
• Log P: -7.167795
• Molar Refractivity: 107.792 cm^3
• Polarizability: 46.10792 Å^3
• Polar Surface Area: 288.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• RTECS: WK1976500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC)
• Loss on Drying: ~5% loss on drying
• Empirical Formula (Hill Notation): C18H37N5O10 · xH2SO4

DETAILS

Sigma Aldrich - B5264

Application
Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene.
Biochem/physiol Actions
Kanamycin B is an aminoglycoside antibiotic that is the 2-amino,2-deoxy-analog of kanamycin A. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasm.

Sigma Aldrich - 60616

Biochem/physiol Actions
Kanamycin B is an aminoglycoside antibiotic that is the 2-amino,2-deoxy-analog of kanamycin A. Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasm.