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

• ChemBase ID: 167465
• Molecular Formular: C26H50N6O15
• Molecular Mass: 686.7064
• Monoisotopic Mass: 686.33341493
• 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)NC(=O)[C@H](CCN)O)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[C@H](N)C(C([C@H]1O[C@H]1OC(CO)[C@H]([C@@H](C1O)NC(=O)[C@H](CCN)O)O)O)O[C@H]1OC(CN)[C@H](C(C1O)O)O)O
• InChI: InChI=1S/C26H50N6O15/c27-3-1-10(34)23(42)31-9-5-8(30)21(46-26-19(40)18(39)16(37)12(6-29)44-26)20(41)22(9)47-25-17(38)14(15(36)13(7-33)45-25)32-24(43)11(35)2-4-28/h8-22,25-26,33-41H,1-7,27-30H2,(H,31,42)(H,32,43)/t8-,9+,10-,11-,12?,13?,14-,15+,16+,17?,18?,19?,20?,21?,22-,25+,26+/m0/s1
• InChIKey: YJEDOCBINAXBLM-ZFLVPIEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(1R,2S,5S)-5-amino-2-{[(2S,4S,5S)-4-[(2S)-4-amino-2-hydroxybutanamido]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• IUPAC Traditional name: (2S)-4-amino-N-[(1R,2S,5S)-5-amino-2-{[(2S,4S,5S)-4-[(2S)-4-amino-2-hydroxybutanamido]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-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)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine; 1,3"-Di-N-(L-4-amino-2-hydroxybutyryl) Kanamycin A; 1,3''-Di-HABA Kanamycin A

Database IDs

• CAS Number: 197909-66-3
• PubChem SID: 162261598
• PubChem CID: 71316091

CALCULATED PROPERTIES

• Acid pKa: 11.83595
• H Acceptors: 19
• H Donor: 15
• LogD (pH = 5.5): -21.838377
• LogD (pH = 7.4): -17.358425
• Log P: -10.107852
• Molar Refractivity: 153.5475 cm^3
• Polarizability: 63.834457 Å^3
• Polar Surface Area: 381.27 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D446380

Kanamycin (K137500) derivative as synthetic byproduct of Amikacin (A578500).

REFERENCES

• Kawaguchi, H., et al.: J. Antibiotics, 25, 695 (1972)
• Naito, T., et al.: J. Antibiotics, 26, 297 (1972)