neomycin   

GtoPdb Ligand ID: 709

Synonyms: Neo-Rx® | neomycin sulfate
neomycin is an approved drug (FDA (1964))
Comment: Neomycin is an aminoglycoside antibiotic. 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.
2D Structure
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Physico-chemical Properties
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
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
Compound class Natural product or derivative
Approved drug? Yes (FDA (1964))
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
International Nonproprietary Names
INN number INN
253 framycetin
Synonyms
Neo-Rx® | neomycin sulfate
Database Links
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
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Search PubMed clinical trials framycetin
Search PubMed titles framycetin
Search PubMed titles/abstracts framycetin
Search UniChem for chemical match using the InChIKey PGBHMTALBVVCIT-VCIWKGPPSA-N
Search UniChem for chemicals with the same backbone PGBHMTALBVVCIT
Wikipedia Neomycin