(2R,4S,5S)-2-{[(2R,6S,8aR)-7-amino-6-{[(2R,3R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol

• ChemBase ID: 160768
• Molecular Formular: C21H41N5O11
• Molecular Mass: 539.57714
• Monoisotopic Mass: 539.28025716
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)O[C@H]1O[C@H]2C(C(C1NC)O)O[C@@H](C(C2)N)OC1[C@@H]([C@H](C(CC1N)N)O)O)O)O)N
• Canonical SMILES: CNC1[C@H](O[C@H]2C(C1O)O[C@@H](C(C2)N)OC1C(N)CC([C@@H]([C@H]1O)O)N)O[C@H]1OC(CO)[C@H]([C@@H](C1O)O)N
• InChI: InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5?,6?,7?,8-,9?,10-,11?,12-,13+,14?,15-,16?,17?,18?,19+,20-,21-/m1/s1
• InChIKey: XZNUGFQTQHRASN-XMXDRTAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-{[(2R,6S,8aR)-7-amino-6-{[(2R,3R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
• IUPAC Traditional name: (2R,4S,5S)-2-{[(2R,6S,8aR)-7-amino-6-{[(2R,3R)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
• Synonyms: O-4-Amino-4-deoxy-α-D-glucopyranosyl-(18)-O-(8R)-2-amino-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranosyl-(14)-2-deoxy-D-streptamineSulfate; Apramycin Sulfate

Database IDs

• CAS Number: 65710-07-8
• PubChem SID: 162254903
• PubChem CID: 71313473

CALCULATED PROPERTIES

• Acid pKa: 12.28959
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -20.033087
• LogD (pH = 7.4): -12.852177
• Log P: -6.5081105
• Molar Refractivity: 120.9143 cm^3
• Polarizability: 51.61567 Å^3
• Polar Surface Area: 283.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: >168°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A729600

Broad spectrum aminocyclitol antibiotic and component of the Nebramycin complex, produced by a strain of Streptomyces tenebrarius. Antibacterial.

REFERENCES

• Thompson, R.Q., et al.: Antimicrob. Agents Chemother., 332 (1967)
• Ryden, R., et al.: J. Antimicrob. Chemother., 3, 609 (1967)
• Smith, P., et al.: Clin. Therap., 23, 1231 (1967)