(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编号: 133030
• 分子式: C21H43N5O15S
• 平均质量: 637.65562
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: apramycin; sulfuric acid
• 别名: Nebramycin II; Apramycin sulfate salt

登记号

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

理论计算性质

• Acid pKa: 12.28959
• 质子受体: 16
• 质子供体: 11
• LogD (pH = 5.5): -20.033087
• LogD (pH = 7.4): -12.852177
• Log P: -6.5081105
• 摩尔折射率: 120.9143 cm^3
• 极化性: 51.61567 Å^3
• 极化表面积: 283.64 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 61-36/38
• 安全公开号: 53-26-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H319-H360
• GHS警示性声明: P201-P305 + P351 + P338-P308 + P313
• 个人保护装置: 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
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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