(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol tris(sulfuric acid) hydrate

• ChemBase ID: 133310
• Molecular Formular: C23H54N6O26S3
• Molecular Mass: 926.89446
• Monoisotopic Mass: 926.22498888
• SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)N)O[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O[C@@H]1C([C@H]([C@@H]([C@@H](O1)CN)O)O)N)O)O)N.O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@@H](CN)[C@H]([C@@H](C1N)O)O)O)O[C@@H]1[C@@H](O)[C@H](N)C[C@@H]([C@H]1O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1N)O)O)N.O
• InChI: InChI=1S/C23H46N6O13.3H2O4S.H2O/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22;3*1-5(2,3)4;/h5-23,30-36H,1-4,24-29H2;3*(H2,1,2,3,4);1H2/t5-,6+,7-,8+,9-,10-,11?,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;;;;/m1..../s1
• InChIKey: WHAGUNPVKDUVFV-QGTTWHFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol tris(sulfuric acid) hydrate
• IUPAC Traditional name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol tris(sulfuric acid) hydrate
• Synonyms: Neomycin trisulfate salt hydrate; 新霉素 三硫酸盐 水合物

Database IDs

• CAS Number: 1405-10-3
• EC Number: 215-773-1
• PubChem SID: 24897532; 162227587
• PubChem CID: 71308654

CALCULATED PROPERTIES

• Acid pKa: 12.291083
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -24.511583
• LogD (pH = 7.4): -15.933928
• Log P: -8.415177
• Molar Refractivity: 135.9003 cm^3
• Polarizability: 58.22208 Å^3
• Polar Surface Area: 353.11 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

DETAILS

Sigma Aldrich - N1876

Biochem/physiol Actions
作用方式：与引起错编的 30S 和 50S（有时为 50S）亚基结合；抑制蛋白质合成的开始和延长。 抗菌谱：革兰氏阴性和革兰氏阳性细菌。
Mode of action: binds to the 30S and in some cases the 50S subunit causing miscoding; inhibits initiation and elongation during protein synthesis. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria. Neomycin blocks voltage-sensitive Ca2+ channels without affecting the Na+/Ca2+ antiporter in neurons.
Caution
Protect from light and moisture.
Application
Neomycin is used in molecular biology as a selection agent for prokaryotic cells that have been transformed using the selectable marker gene (neo). It is also used to study ototoxic side effects of antibiotics, platelet-derived growth factor (PDGF) responses in C3H/10T1/2 C18 fibroblasts, and extraction of Nuclear Phosphatidylinositol 4,5-Bisphosphate-Interacting Proteins 1,2,3. Product N1876 is supplied as a powder.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information