(2S,3R,4S,5S,6R)-4-amino-2-{[(1R,2R,3S,4R,6S)-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: 172036
• Molecular Formular: C18H39N5O14S
• Molecular Mass: 581.59236
• Monoisotopic Mass: 581.22142195
• SMILES: [C@@H]1([C@@H](C[C@@H]([C@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)CO)O)N)O)N)N)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1N)O)O)CN.S(=O)(=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-;/m1./s1
• InChIKey: YGTPKDKJVZOVCO-BIYMZBHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-4-amino-2-{[(1R,2R,3S,4R,6S)-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-{[(1R,2R,3S,4R,6S)-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: O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-D-streptamine Sulfate; Aminodeoxykanamycin Sulfate; Bekanamycin Sulfate; Kanamycin B Sulfate; Kanendomycin Sulfate; Kanamycin B Sulfate

Database IDs

• CAS Number: 29701-07-3
• PubChem SID: 164227946
• PubChem CID: 71749665

CALCULATED PROPERTIES

• 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
• Acid pKa: 12.488072
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -20.649662
• LogD (pH = 7.4): -13.571994

DETAILS

Toronto Research Chemicals - K137515

Antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.

REFERENCES

• Ito, et al.: J. Antibiot., 17, 189 (1964)
• Toda, S., et al.: J. Antibiot., 30, 1002 (1964)
• Claes, P.J., et al.: Anal. Profiles Drug. Subs., 6, 259 (1964)