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

• ChemBase ID: 169824
• Molecular Formular: C22H43N5O13
• Molecular Mass: 585.60252
• Monoisotopic Mass: 585.28573646
• SMILES: [C@@H]1([C@@H](C[C@@H](C(C1O)O[C@@H]1C(C([C@@H](C(O1)CN)O)O)O)N)N)O[C@H]1OC([C@H]([C@@H](C1O)NC(=O)[C@H](CCN)O)O)CO
• Canonical SMILES: NCC[C@@H](C(=O)N[C@@H]1C(O)[C@H](OC([C@H]1O)CO)O[C@H]1[C@H](N)C[C@@H](C(C1O)O[C@H]1OC(CN)[C@H](C(C1O)O)O)N)O
• InChI: InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-11-12(30)10(5-28)38-21(14(11)32)39-18-6(25)3-7(26)19(17(18)35)40-22-16(34)15(33)13(31)9(4-24)37-22/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8+,9?,10?,11+,12-,13-,14?,15?,16?,17?,18+,19?,21-,22-/m1/s1
• InChIKey: VVJDZJSGQOGXFX-VJILDFPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(2S,4S,5S)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]-2-hydroxybutanamide
• IUPAC Traditional name: (2S)-4-amino-N-[(2S,4S,5S)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]-2-hydroxybutanamide
• Synonyms: O-6-Amino-6-deoxy-α-D-glucopyranosyl-(1→4)-O-[3-[[(2S)-4-amino-2-hydroxy-1-oxobutyl]amino]-3-deoxy-α-D-glucopyranosyl-(1→6)]-2-deoxy-D-streptamine; Antibiotic BB-K 11; 3’’-N-[L-(-)-γ-Amino-α-hydroxybutyryl]kanamycin A; 3''-HABA Kanamycin A

Database IDs

• CAS Number: 50725-25-2
• PubChem SID: 162263956
• PubChem CID: 71317184

CALCULATED PROPERTIES

• Acid pKa: 11.916297
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -19.73159
• LogD (pH = 7.4): -14.926037
• Log P: -8.584383
• Molar Refractivity: 129.841 cm^3
• Polarizability: 54.552784 Å^3
• Polar Surface Area: 331.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H011750

Amikacin (A578500) impurity C (EP).

REFERENCES

• Naito, T., et al.: J. Antibiot., 26, 297 (1973)
• Weber, A., et al.: Clin. Microbiol., 21, 419 (1973)