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Neomycin

July 24, 2017
Common Name

Neomycin Description

A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). Neomycin is a bactericidal aminoglycoside antibiotic that binds to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and acceptor tRNA sites and reslits in the production of non-functional or toxic peptides. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Fradiomycin bChEBI FramicetinaChEBI FramycetineChEBI FramycetinumChEBI Neomycin bChEBI Caswell no. 595HMDB Neomycin b slifateHMDB Neomycin slifateHMDB Neomycin sliphateHMDB USAF CB-19HMDB Fradiomycin slifateMeSH Neomycin palmitateMeSH Palmitate, neomycinMeSH Slifate, neomycinMeSH Slifate, fradiomycinMeSH

Chemical Formlia

C23H46N6O13 Average Molecliar Weight

614.6437 Monoisotopic Molecliar Weight

614.312285588 IUPAC Name

(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-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol Traditional Name

neomycin CAS Registry Number

1404-04-2 SMILES

NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H46N6O13/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/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

InChI Key

PGBHMTALBVVCIT-VCIWKGPPSA-N Chemical Taxonomy 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. Kingdom

Organic compounds Super Class

Organic oxygen compounds Class

Organooxygen compounds Sub Class

Carbohydrates and carbohydrate conjugates Direct Parent

4,5-disubstituted 2-deoxystreptamines Alternative Parents

  • O-glycosyl compounds
  • Disaccharides
  • Aminocyclitols and derivatives
  • Cyclohexylamines
  • Cyclohexanols
  • Oxanes
  • Tetrahydrofurans
  • 1,2-aminoalcohols
  • Oxacyclic compounds
  • Acetals
  • Primary alcohols
  • Organopnictogen compounds
  • Monoalkylamines
  • Hydrocarbon derivatives

    • Substituents

  • 4,5-disubstituted 2-deoxystreptamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Cyclitol or derivatives
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • aminoglycoside (CHEBI:7508 )
  • 2-Deoxystreptamines (C01737 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Aminoglycosides
  • Anti-Bacterial Agents
  • Antibiotics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point6 °C (slifate form)Not Available Boiling PointNot AvailableNot Available Water Solubility6.47e+01 g/LNot Available LogP-7.8Not Available

    Predicted Properties

    Property Value Source Water Solubility64.7 mg/mLALOGPS logP-2.8ALOGPS logP-8.4ChemAxon logS-0.98ALOGPS pKa (Strongest Acidic)12.29ChemAxon pKa (Strongest Basic)9.97ChemAxon Physiological Charge6ChemAxon Hydrogen Acceptor Count19ChemAxon Hydrogen Donor Count13ChemAxon Polar Surface Area353.11 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity135.9 m3·mol-1ChemAxon Polarizability60.87 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Neomycin PathwaySMP00256Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00994

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00994

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-2 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00994 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    8075 KEGG Compound ID

    C01737 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Neomycin NuGOwiki Link

    HMDB15129 Metagene Link

    HMDB15129 METLIN ID

    Not Available PubChem Compound

    8378 PDB ID

    NMY ChEBI ID

    7508

    Product: CPI-170

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 11594239

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