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

• ChemBase ID: 169823
• 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)NC(=O)[C@H](CCN)O)N)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@@H](C(C1O[C@H]1OC(CN)[C@H](C(C1O)O)O)O)O[C@H]1OC(CO)[C@H]([C@@H](C1O)N)O)O
• InChI: InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-21-14(32)11(26)12(30)10(5-28)38-21)17(35)19(7)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: OTDUEYVCDKBDRQ-VJILDFPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(1S,4S,5R)-5-amino-4-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• IUPAC Traditional name: (2S)-4-amino-N-[(1S,4S,5R)-5-amino-4-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[(2R,5S)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• Synonyms: (S)-O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-amino-6-deoxy-α-D-glucopyranosyl-(1→4)]-N3-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptamine; BB-K29; 3-N-[L-(-)-γ-Amino-α-hydroxybutyryl]kanamycin A; 3-HABA Kanamycin A

Database IDs

• CAS Number: 50725-24-1
• PubChem SID: 162263955
• PubChem CID: 71317183

CALCULATED PROPERTIES

• Acid pKa: 12.107323
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -20.16644
• LogD (pH = 7.4): -15.09928
• 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: Off-White Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H011745

Amikacin (A578500) impurity A.

REFERENCES

• Gunawardana, G., et al.: J. Antibiot., 50, 887 (1997)