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

• ChemBase ID: 156303
• Molecular Formular: C22H47N5O15
• Molecular Mass: 621.63308
• Monoisotopic Mass: 621.30686583
• SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1NC(=O)C(CCN)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)O)N.O.O
• Canonical SMILES: NCCC(C(=O)N[C@H]1C[C@@H](N)[C@@H]([C@H]([C@@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O.O.O
• InChI: InChI=1S/C22H43N5O13.2H2O/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);2*1H2/t6-,7+,8?,9-,10-,11+,12-,13-,14-,15+,16-,17-,18+,19-,21-,22-;;/m1../s1
• InChIKey: ARXXWSPWNHULSJ-WNAAXDCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-[(1S,2R,3R,4S,5R)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide dihydrate
• IUPAC Traditional name: 4-amino-N-[(1S,2R,3R,4S,5R)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide dihydrate
• Synonyms: N1-[(S)-4-Amino-2-hydroxybutyryl]-kanamycin A; Amikacin dihydrate

Database IDs

• CAS Number: 37517-28-5
• EC Number: 253-538-5
• MDL Number: MFCD00151224
• Beilstein Number: 1445422
• PubChem SID: 162250441
• PubChem CID: 45051573

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: H2O: soluble50 mg/mL, clear, colorless
• Optical Rotation: [α]20/D +93±2°, c = 2% in H2O

Safety Information

• RTECS: WK1955000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C22H43N5O13 · 2H2O

DETAILS

Sigma Aldrich - 06568

Other Notes
Aminoglycoside antibiotic1