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

• ChemBase ID: 103007
• Molecular Formular: C22H43N5O13
• Molecular Mass: 585.60252
• Monoisotopic Mass: 585.28573646
• SMILES: NCCC(O)C(=O)NC1CC(N)C(OC2OC(CN)C(O)C(O)C2O)C(O)C1OC1OC(CO)C(O)C(N)C1O
• Canonical SMILES: NCCC(C(=O)NC1CC(N)C(C(C1OC1OC(CO)C(C(C1O)N)O)O)OC1OC(CN)C(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)
• InChIKey: LKCWBDHBTVXHDL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5-amino-2-{[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl)-2-hydroxybutanamide
• IUPAC Traditional name: @amikacin
• Synonyms: 1-N-[L(-)-4-Amino-2-hydroxy-butyryl] kanamycin A; AMIKACIN; AMIKACIN, U.S.P.

Database IDs

• CAS Number: 37517-28-5
• EC Number: 253-538-5
• PubChem SID: 162089800
• PubChem CID: 2142

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

• Melting Point: 214°C

Safety Information

• Storage Condition: 2-8°C, Desiccate
• RTECS: WK1955000

Product Information

• Grade: TECHNICAL; USP

DETAILS

MP Biomedicals - 02199887

Technical Grade(N1-[(s)-4-Amino-2-hydroxybutyryl]kanamycin A) From Kanamycin A White crystalline powder

MP Biomedicals - 02150342

From Kanamycin A
m.p. 203-204°C
White crystalline powder