benzyl N-{[(3S,6R)-6-{[(3S,4R,6S)-4,6-diamino-3-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}carbamate

• ChemBase ID: 161748
• Molecular Formular: C26H42N4O13
• Molecular Mass: 618.63068
• Monoisotopic Mass: 618.27483742
• SMILES: [C@@H]1([C@@H](C[C@@H](C(C1O)O[C@@H]1C(C([C@@H](C(O1)CNC(=O)OCc1ccccc1)O)O)O)N)N)O[C@H]1OC([C@H]([C@@H](C1O)N)O)CO
• Canonical SMILES: OCC1O[C@H](O[C@H]2[C@H](N)C[C@@H](C(C2O)O[C@H]2OC(CNC(=O)OCc3ccccc3)[C@H](C(C2O)O)O)N)C([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C26H42N4O13/c27-11-6-12(28)23(21(37)22(11)42-24-18(34)15(29)16(32)14(8-31)41-24)43-25-20(36)19(35)17(33)13(40-25)7-30-26(38)39-9-10-4-2-1-3-5-10/h1-5,11-25,31-37H,6-9,27-29H2,(H,30,38)/t11-,12+,13?,14?,15+,16-,17-,18?,19?,20?,21?,22+,23?,24-,25-/m1/s1
• InChIKey: AJGFIHSSLBJYBS-OBFUEHGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{[(3S,6R)-6-{[(3S,4R,6S)-4,6-diamino-3-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}carbamate
• IUPAC Traditional name: benzyl N-{[(3S,6R)-6-{[(3S,4R,6S)-4,6-diamino-3-{[(2S,4S,5S)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}carbamate
• Synonyms: 6'-Carbobenzoxykanamycin A; 6'-N-(Benzyloxycarbonyl)kanamycin; O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-deoxy-6-[[(phenylmethoxy)carbonyl]amino]-α-D-glucopyranosyl-(1→4)]-2-deoxy-D-streptamine; 6'-N-(Benzyloxycarbonyl)kanamycin A

Database IDs

• CAS Number: 40372-09-6
• PubChem SID: 162255883
• PubChem CID: 71313880

CALCULATED PROPERTIES

• Acid pKa: 12.068307
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -13.052769
• LogD (pH = 7.4): -9.100654
• Log P: -4.8983026
• Molar Refractivity: 141.8145 cm^3
• Polarizability: 58.898212 Å^3
• Polar Surface Area: 294.92 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - B286090

Used in the synthesis of Amikacin (A578500) derivatives.

REFERENCES

• Matsuda, K. et al.: J. Antibiot. 39, 1479 (1986)