ChemSpider 2D Image | Apramycin | C21H41N5O11

Apramycin

  • Molecular FormulaC21H41N5O11
  • Average mass539.577 Da
  • Monoisotopic mass539.280273 Da
  • ChemSpider ID2339128
  • defined stereocentres - 17 of 17 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2R,3R,4S,5S,6S)-5-Amino-2-{[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (non-preferred name)
(2R,3S,4R,4aR,6S,7R,8aS)-7-Amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl 4-amino-4-deoxy-α-D-glucopyranoside [ACD/IUPAC Name]
(2R,3S,4R,4aR,6S,7R,8aS)-7-Amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl-4-amino-4-desoxy-α-D-glucopyranosid [German] [ACD/IUPAC Name]
253-460-1 [EINECS]
3185
37321-09-8 [RN]
4-Amino-4-désoxy-α-D-glucopyranoside de (2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(méthylamino)octahydropyrano[3,2-b]pyran-2-yle [French] [ACD/IUPAC Name]
4-O-[3a-Amino-6a-[(4-amino-4-deoxy-a-D-glucopyranosyl)oxy]-2,3,4,4ab,6,7,8aa-octahydro-8b-hydroxy-7b-(methylamino)pyranopyrano[3,2-b]pyran-2a-yl]-2-deoxy-D-streptamine
Ambylan [Trade name]
Apralan [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

388K3TR36Z [DBID]
EL 857 [DBID]
UNII-388K3TR36Z [DBID]
CCRIS 937 [DBID]
UNII:388K3TR36Z [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An aminoglycoside that is 2-deoxystreptamine that is substituted on the oxygen at position 4 by an (8<stereo>R</stereo>)-2-amino-8-<element>O</element>-(4-amino-4-deoxy-<stereo>alpha</stereo>-<stereo> D</stereo>-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-<stereo>D</stereo>-glycero-<stereo>alpha</stereo>-<stereo>D</stereo>-<stereo>allo</stereo>-octodialdo-1,5:8,4-dipyranos-1-yl) group. ChEBI CHEBI:2790
    • Bio Activity:

      Antibacterial MedChem Express HY-17558
      Anti-infection MedChem Express HY-17558
      Anti-infection; MedChem Express HY-17558
      Apramycin(Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. MedChem Express http://www.medchemexpress.com/Cysteine-Protease-inhibitor.html, HY-17558
      Apramycin(Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. ;IC50 value:;Target: Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria. MedChem Express HY-17558

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.6±0.1 g/cm3
Boiling Point: 823.0±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 136.1±6.0 kJ/mol
Flash Point: 451.6±34.3 °C
Index of Refraction: 1.658
Molar Refractivity: 126.8±0.4 cm3
#H bond acceptors: 16
#H bond donors: 15
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 3
ACD/LogP: -2.45
ACD/LogD (pH 5.5): -10.32
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -7.55
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 284 Å2
Polarizability: 50.3±0.5 10-24cm3
Surface Tension: 93.0±5.0 dyne/cm
Molar Volume: 344.4±5.0 cm3

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