(2S)-4-amino-N-[(1R,2S,5S)-5-amino-2-{[(2S,4S,5S)-4-amino-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: 159785
• 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)NC(=O)[C@H](CCN)O)O[C@H]1OC([C@H]([C@@H](C1O)N)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)N)O)O)O[C@H]1OC(CN)[C@H](C(C1O)O)O)O
• InChI: InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/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+/m0/s1
• InChIKey: LKCWBDHBTVXHDL-TVSSMWSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(1R,2S,5S)-5-amino-2-{[(2S,4S,5S)-4-amino-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-amino-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-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-amino-6-deoxy-α-D-glucopyranosyl-(1→4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine Sulfate; 1-N-[L-(-)-γ-Amino-α-hydroxybutyryl]kanamycin A Sulfate; Amiglyde V; Amika; Amikacin Disulfate; Amikacin Sulfate; Amikavet; Amikin; Amiklin; Antibiotic BB-K 8 Sulfate; Biklin; Biodacyn; Biodacyna; Fabianol; Grasil; Kaminax; Mikavir; Novamin; Pierami; Selemycin; Amikacin Sulfate

Database IDs

• CAS Number: 39831-55-5
• PubChem SID: 162253920
• PubChem CID: 71313137

CALCULATED PROPERTIES

• Acid pKa: 12.104234
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -20.16644
• LogD (pH = 7.4): -15.099279
• 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

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >210°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A578500

Semisynthetic aminoglycoside antibiotic derived from Kanamycin A. Antibacterial.

REFERENCES

• Cabana, T., et al.: Antimicrob. Agents Chemother., 3, 478 (1973)
• Cappelletti, L.M., et al.: J. Antibiot., 36, 328 (1973)
• Monteleone, P.M., et al.: Anal. Profiles Drug Subs., 12, 37 (1973)