(2R,3R,4S,5S,6S)-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}-5-amino-6-(hydroxymethyl)oxane-3,4-diol; sulfuric acid

• ChemBase ID: 133030
• Molecular Formular: C21H43N5O15S
• Molecular Mass: 637.65562
• Monoisotopic Mass: 637.2476367
• SMILES: CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O)N)N)N)O[C@@H]1O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)N)O)O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
• InChI: InChI=1S/C21H41N5O11.H2O4S/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;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1
• InChIKey: WGLYHYWDYPSNPF-RQFIXDHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6S)-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}-5-amino-6-(hydroxymethyl)oxane-3,4-diol; sulfuric acid
• IUPAC Traditional name: apramycin; sulfuric acid
• Synonyms: Nebramycin II; Apramycin sulfate salt

Database IDs

• CAS Number: 65710-07-8
• EC Number: 265-890-7
• MDL Number: MFCD06200257
• PubChem SID: 162227307
• PubChem CID: 3081544

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

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-36/38
• Safety Statements: 53-26-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H360
• GHS Precautionary statements: P201-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (TLC)
• Impurities: ≤10% water
• Empirical Formula (Hill Notation): C21H41N5O11 · xH2SO4

DETAILS

Sigma Aldrich - A2024

Application
Apramycin is used to study antibiotic resistance 1,2 as well as protein synthesis translocation-step inhibition in bacteria and prokaryotes.
Apramycin is used to study protein synthesis translocation-step inhibition in bacteria and prokaryotes.
Biochem/physiol Actions
Apramycin inhibits protein synthesis by blocking translocation. It is also able to bind to the eukaryotic decoding site 3.

Sigma Aldrich - 10816

Other Notes
Effects on bacterial protein synthesis1