arbekacin   

GtoPdb Ligand ID: 7345

Synonyms: arbekacin sulfate | ME1100 | NPC-14
Comment: Arbekacin is a semisynthetic aminoglycoside antibiotic that has activity against both gram-positive and gram-negative bacteria [2]. Several aminoglycoside antibiotics have been reported to have the ability to promote mRNA translation even in the presence of premature termination codons (PTCs) in mutated genes. In the absence of pharmaceutical intervention, the ribosomal translation process produces truncated, often non-functional protein products. However, in the presence of such compounds the ribosomes 'readthrough' the PTCs, producing increased amounts of full-length, functional protein. This developing pharmaceutical intervention has been termed 'readthrough strategy'.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 16
Hydrogen bond donors 11
Rotatable bonds 11
Topological polar surface area 297.27
Molecular weight 552.31
XLogP -5.86
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES NCCC(C(=O)NC1CC(N)C(C(C1OC1OC(CO)C(C(C1O)N)O)O)OC1OC(CN)CCC1N)O
Isomeric SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)CC[C@H]1N)O
InChI InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
InChI Key MKKYBZZTJQGVCD-XTCKQBCOSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
International Nonproprietary Names
INN number INN
5914 arbekacin
Synonyms
arbekacin sulfate | ME1100 | NPC-14
Database Links
Specialist databases
AntibioticDB 3
Other databases
CAS Registry No. 51025-85-5 (source: Scifinder)
ChEBI CHEBI:37922
ChEMBL Ligand CHEMBL426926
DrugBank Ligand DB06696
DrugCentral Ligand 235
GtoPdb PubChem SID 178103917
PubChem CID 68682
RCSB PDB Ligand 84G
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Wikipedia Arbekacin