iboxamycin   Click here for help

GtoPdb Ligand ID: 11790

Synonyms: IBX | OPP-3
Compound class: Synthetic organic
Comment: Iboxamycin (OPP-3) is an orally bioavailable, synthetic antibacterial compound [1]. Structurally, IBX is built on a oxepanoproline scaffold that is linked to the aminooctose residue of clindamycin. X-ray crystallography shows that IBX binds to the large ribosomal subunit in the bacteria (more effectively than clindamycin) and disrupts translation initiation. Iboxamycin is a novel broad-spectrum agent that is active against Gram-positive and Gram-negative bacteria including ESKAPE pathogens that express resistance-conferring Erm and Cfr ribosomal RNA methyltransferase enzymes.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 145.58
Molecular weight 494.22
XLogP 2.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CSC1O[C@@H]([C@@H]([C@@H](Cl)C)NC(=O)[C@H]2NC[C@H]3[C@H]2OCC[C@H](C3)CC(C)C)C([C@H]([C@H]1O)O)O
Isomeric SMILES [C@H]12CN[C@H](C(=O)N[C@H]([C@H](C)Cl)[C@@H]3OC(SC)[C@H](O)[C@H](O)C3O)[C@@H]1OCC[C@@H](CC(C)C)C2
InChI InChI=1S/C22H39ClN2O6S/c1-10(2)7-12-5-6-30-19-13(8-12)9-24-15(19)21(29)25-14(11(3)23)20-17(27)16(26)18(28)22(31-20)32-4/h10-20,22,24,26-28H,5-9H2,1-4H3,(H,25,29)/t11-,12-,13-,14+,15-,16+,17?,18+,19+,20-,22?/m0/s1
InChI Key JPCLUJPDWMBCAA-ALYUFWCISA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4S,5aS,8S,8aR)-N-[(1S,2S)-2-chloro-1-[(2S,4R,5R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-(2-methylpropyl)-octahydro-2H-oxepino[2,3-c]pyrrole-8-carboxamide
Synonyms Click here for help
IBX | OPP-3
Database Links Click here for help
GtoPdb PubChem SID 458923825
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