(2S)-4-amino-N-[(1R,4R,5R)-5-amino-2-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4R,5S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide

• ChemBase ID: 159787
• Molecular Formular: C22H44N6O12
• Molecular Mass: 584.61776
• Monoisotopic Mass: 584.30172088
• SMILES: C1([C@@H]([C@H](C[C@H](C1O[C@H]1OC([C@H]([C@@H](C1O)N)O)CO)NC(=O)[C@H](CCN)O)N)O[C@H]1OC([C@H]([C@@H](C1N)O)O)CN)O
• Canonical SMILES: NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H](C(C1O[C@H]1OC(CO)[C@H]([C@@H](C1O)N)O)O)O[C@H]1OC(CN)[C@H]([C@@H](C1N)O)O)O
• InChI: InChI=1S/C22H44N6O12/c23-2-1-8(30)20(36)28-7-3-6(25)18(39-21-12(27)15(33)14(32)9(4-24)37-21)17(35)19(7)40-22-16(34)11(26)13(31)10(5-29)38-22/h6-19,21-22,29-35H,1-5,23-27H2,(H,28,36)/t6-,7-,8+,9?,10?,11+,12?,13-,14-,15-,16?,17?,18-,19?,21-,22-/m1/s1
• InChIKey: YISFONZWEZUXDI-OUGKPOERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(1R,4R,5R)-5-amino-2-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4R,5S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• IUPAC Traditional name: (2S)-4-amino-N-[(1R,4R,5R)-5-amino-2-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4R,5S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• Synonyms: O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl-(1→4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine; 1-N-[(S)-4-Amino-2-hydroxybutyryl]kanamycin B; BB-K26; Habekacin; Amikacin B

Database IDs

• CAS Number: 48237-20-3
• PubChem SID: 162253922
• PubChem CID: 71313139

CALCULATED PROPERTIES

• Acid pKa: 12.4818
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -22.756454
• LogD (pH = 7.4): -16.004496
• Log P: -8.691264
• Molar Refractivity: 131.4985 cm^3
• Polarizability: 55.38792 Å^3
• Polar Surface Area: 337.73 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A578515

Amikacin (A578500) impurity, as a new aminoglycoside antibiotic.

REFERENCES

• Jung, F., et al.: J. Med. Chem., 34, 1110 (1991}, Choi, K., et al.: J. Antimicrob. Chemother., 39, 509 (1997)
• Galimand, M., et al.: Antimicrob. Agents Chemother., 47, 2565 (1997)