neomycin   Click here for help

GtoPdb Ligand ID: 709

Synonyms: Neo-Rx® | neomycin sulfate
Approved drug PDB Ligand
neomycin is an approved drug (FDA (1964))
Compound class: Natural product or derivative
Comment: Neomycin is an aminoglycoside antibacterial. Neomycin is active against Gram-negative bacteria, and partially active against Gram-positive bacteria. Standard grade neomycin is a mixture of several related compounds, including neomycin A (neamine), neomycin B (framycetin) and neomycin C, with neomycin B being the most active component. We show the structure of neomycin B here.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 19
Hydrogen bond donors 13
Rotatable bonds 9
Topological polar surface area 353.11
Molecular weight 614.31
XLogP -6.91
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC1OC(C(C1OC1OC(CN)C(C(C1N)O)O)O)OC1C(O)C(N)CC(C1OC1OC(CN)C(C(C1N)O)O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@@H](CN)[C@H]([C@@H]([C@H]1N)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
InChI 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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1964))
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
253 framycetin
Synonyms Click here for help
Neo-Rx® | neomycin sulfate
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Neomycin, Fradiomycin
GPCRdb Ligand neomycin
Other databases
BindingDB Ligand 19
CAS Registry No. 119-04-0 (source: ChEBI)
ChEBI CHEBI:7508
ChEMBL Ligand CHEMBL184618
DrugBank Ligand DB00994
DrugCentral Ligand 1896
GtoPdb PubChem SID 135652707
PubChem CID 8378
RCSB PDB Ligand NMY
Search Google for chemical match using the InChIKey PGBHMTALBVVCIT-VCIWKGPPSA-N
Search Google for chemicals with the same backbone PGBHMTALBVVCIT
Search PubMed clinical trials framycetin
Search PubMed titles framycetin
Search PubMed titles/abstracts framycetin
UniChem Compound Search for chemical match using the InChIKey PGBHMTALBVVCIT-VCIWKGPPSA-N
UniChem Connectivity Search for chemical match using the InChIKey PGBHMTALBVVCIT-VCIWKGPPSA-N
Wikipedia Neomycin