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| Synonyms | (2S,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((2R,3S,4R,5S)-5-(((1R,2R,3S,5R,6S)-3,5-diamino-2-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-hydroxycyclohexyl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)ox |
|---|---|
| Specifications & Purity | ≥97% |
| Biochemical and Physiological Mechanisms | Neomycin sulfate is an aminoglycoside antibiotic, used to treat bacteria infections. |
| Storage Temp | Protected from light,Store at -20°C,Argon charged |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
Information Neomycin sulfate is an aminoglycoside antibiotic , used to treat bacteria infections. In vitro Neomycin interacts preferentially with the ribozyme-substrate complex and that this interaction leads to a reduction in the cleavage rate by stabilizing the ground state of the complex and destabilizing the transition state of the cleavage step. Neomycin effects a conformational change in the structure of trans-activating region (TAR) that can be detected by circular dichroism spectroscopy. Neomycin acts as a noncompetitive inhibitor that can bind to the Tat-TAR complex and increase the rate constant (koff) for dissociation of the peptide from the RNA. Neomycin is the most effective aminoglycoside (groove binder) in stabilizing a DNA triple helix. Neomycin stabilizes TAT, as well as mixed base DNA triplexes, better than known DNA minor groove binders (which usually destabilize the triplex) and polyamines. Neomycin shows a preference for stabilization of TAT triplets but can also accommodate CGC(+) triplets. Neomycin induces a concentration- and voltage-dependent partial block from both the cytosolic and luminal faces of the channel. Neomycin has a greater affinity for the luminal site of interaction than the cytosolic site: zero-voltage dissociation constants (Kb(0)) are respectively 210.20 nM and 589.70 nM for luminal and cytosolic block. Neomycin also exhibits voltage-dependent relief of block at holding potentials >+60 mV. |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Aminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides |
| Direct Parent | 4,5-disubstituted 2-deoxystreptamines |
| Alternative Parents | Disaccharides O-glycosyl compounds Aminocyclitols and derivatives Cyclohexanols Cyclohexylamines Organic sulfuric acids Oxanes Tetrahydrofurans 1,2-aminoalcohols Acetals Oxacyclic compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Primary alcohols Organopnictogen compounds |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | 4,5-disubstituted 2-deoxystreptamine - Disaccharide - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Sulfuric acid - Cyclitol or derivatives - Oxane - Cyclic alcohol - Tetrahydrofuran - Organic sulfuric acid or derivatives - Secondary alcohol - 1,2-aminoalcohol - Acetal - Organoheterocyclic compound - Oxacycle - Alcohol - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Amine - Organonitrogen compound - Primary amine - Primary alcohol - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions. |
| External Descriptors | aminoglycoside sulfate salt |
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| Pubchem Sid | 488188580 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488188580 |
| 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,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid |
| INCHI | InChI=1S/C23H46N6O13.H2O4S/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;1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1 |
| InChIKey | OIXVKQDWLFHVGR-WQDIDPJDSA-N |
| Smiles | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N.OS(=O)(=O)O |
| Isomeric SMILES | C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N.OS(=O)(=O)O |
| WGK Germany | 3 |
| RTECS | QP4375000 |
| Molecular Weight | 908.88 (anhydrous basis) |
| Reaxy-Rn | 25082604 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25082604&ln= |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Jan 06, 2025 | N412785 | |
| Certificate of Analysis | Jan 06, 2025 | N412785 | |
| Certificate of Analysis | Jan 06, 2025 | N412785 | |
| Certificate of Analysis | Jan 06, 2025 | N412785 | |
| Certificate of Analysis | Sep 09, 2024 | N412785 | |
| Certificate of Analysis | Sep 09, 2024 | N412785 | |
| Certificate of Analysis | Sep 09, 2024 | N412785 | |
| Certificate of Analysis | Sep 09, 2024 | N412785 | |
| Certificate of Analysis | Sep 09, 2024 | N412785 | |
| Certificate of Analysis | May 20, 2024 | N412785 | |
| Certificate of Analysis | May 20, 2024 | N412785 | |
| Certificate of Analysis | May 20, 2024 | N412785 | |
| Certificate of Analysis | May 20, 2024 | N412785 | |
| Certificate of Analysis | Sep 27, 2023 | N412785 | |
| Certificate of Analysis | Sep 27, 2023 | N412785 | |
| Certificate of Analysis | Sep 27, 2023 | N412785 | |
| Certificate of Analysis | Sep 27, 2023 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 | |
| Certificate of Analysis | Jul 28, 2022 | N412785 |
| Solubility | Solubility (25°C) In vitro Water: 100 mg/mL (140.3 mM); DMSO: Insoluble; Ethanol: Insoluble; |
|---|---|
| Sensitivity | light & moisture sensitive |
| Specific Rotation[α] | 56° (C=10,H2O) |
| Molecular Weight | 712.700 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 15 |
| Hydrogen Bond Acceptor Count | 23 |
| Rotatable Bond Count | 9 |
| Exact Mass | 712.28 Da |
| Monoisotopic Mass | 712.28 Da |
| Topological Polar Surface Area | 436.000 Ų |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Complexity | 953.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 19 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |
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