Neomycin sulfate - PharmPure™, USP, 600 I.U./mg , CAS No.1405-10-3

CAS: 1405-10-3 Cat. No.: N109017 Formula: C₂₃H₄₆N₆O₁₃·3H₂SO₄·xH₂O Molecular Weight: 908.88 (anhydrous basis) EC Number: 215-773-1

GRADE & PURITY PharmPure™, USP, 600 I.U./mg

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

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Neomycin Trisulfate is produced by Streptomyces containing a minimum of 85% neomycin B. It has been used as a selection agent for prokaryotic cells transformed using the neo selectable marker gene, and to study ototoxic side effects of antibiotics, platelet-derived growth factor responses in certain fibroblasts, and extraction of Nuclear Phosphatidylinositol 4,5-Bisphosphate-Interacting Proteins. It is recommended for use in cell culture applications at 50 mg/L.

Specifications

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

PharmPure™, USP, 600 I.U./mg

Biochemical and Physiological Mechanisms

Mode of action: This product acts by binding to the 30S and 50S subunits, causing miscoding and inhibiting initiation and elongation during protein synthesis. Neomycin also blocks voltage-sensitive Ca2+ channels without affecting the Na+/Ca2+ antiporter i

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

PharmPure™, USP

Names and Identifiers

Pubchem Sid

508815346

Canonical 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

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

InChIKey

OIXVKQDWLFHVGR-WQDIDPJDSA-N

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

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=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides
              • Level8 2-deoxystreptamine aminoglycosides
                • Level9 4,5-disubstituted 2-deoxystreptamines

• 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water
• Sensitivity: Light & Moisture sensitive.
• Specific Rotation[α]: 56° (C=10,H2O)
• Molecular Weight: 712.700 g/mol
• 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

XLogP3