N-{[(2R,3S,4S,5R,6R)-6-{[(1R,2R,3S,4R,6S)-4,6-diacetamido-3-{[(2S,3R,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}acetamide

• ChemBase ID: 178222
• Molecular Formular: C26H44N4O15
• Molecular Mass: 652.64536
• Monoisotopic Mass: 652.28031673
• 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)CNC(=O)C)O)O)O)NC(=O)C)NC(=O)C)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)NC(=O)C)O)CO
• Canonical SMILES: OC[C@@H]1O[C@H](O[C@H]2[C@H](NC(=O)C)C[C@@H]([C@H]([C@H]2O)O[C@H]2O[C@H](CNC(=O)C)[C@H]([C@H]([C@H]2O)O)O)NC(=O)C)[C@H]([C@H]([C@@H]1O)NC(=O)C)O
• InChI: InChI=1S/C26H44N4O15/c1-8(32)27-6-14-18(37)20(39)21(40)26(42-14)45-24-13(29-10(3)34)5-12(28-9(2)33)23(22(24)41)44-25-19(38)16(30-11(4)35)17(36)15(7-31)43-25/h12-26,31,36-41H,5-7H2,1-4H3,(H,27,32)(H,28,33)(H,29,34)(H,30,35)/t12-,13+,14-,15-,16+,17-,18-,19-,20+,21-,22-,23+,24-,25-,26-/m1/s1
• InChIKey: GWGDIANBIMNRQW-OBHSWUIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2R,3S,4S,5R,6R)-6-{[(1R,2R,3S,4R,6S)-4,6-diacetamido-3-{[(2S,3R,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}acetamide
• IUPAC Traditional name: N-{[(2R,3S,4S,5R,6R)-6-{[(1R,2R,3S,4R,6S)-4,6-diacetamido-3-{[(2S,3R,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}acetamide
• Synonyms: 4-[O-3-Acetamido-3-deoxy-α-D-glucopyranosyl-6-O-[6-acetamido-6-deoxy-α-D-glucopyranosyl]-N,N'-diacetyl-2-deoxy-L-streptamine; 6-[O-3-Acetamido-3-deoxy-α-D-glucopyranosyl-4-O-[6-acetamido-6-deoxy-α-D-glucopyranosyl]-N,N'-diacetyl-2-deoxy-L-streptamine; Tetra-N-acetyl Kanamycin A

Database IDs

• CAS Number: 20399-23-9
• PubChem SID: 164234132
• PubChem CID: 71752393

CALCULATED PROPERTIES

• Acid pKa: 11.970435
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -7.785527
• LogD (pH = 7.4): -7.7855387
• Log P: -7.785527
• Molar Refractivity: 143.9097 cm^3
• Polarizability: 59.008305 Å^3
• Polar Surface Area: 294.93 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T282570

Protected Kanamycin A (K137500). 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)