eritoran

Ligand id: 4919

Name: eritoran

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 21
Hydrogen bond donors 7
Rotatable bonds 61
Topological polar surface area 313.25
Molecular weight 1312.84
XLogP 16.43
No. Lipinski's rules broken 4

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6R)-4-decoxy-3-hydroxy-5-(3-oxotetradecanoylamino)-6-phosphonooxyoxan-2-yl]methoxy]-4-[(3R)-3-methoxydecoxy]-2-(methoxymethyl)-5-[[(Z)-octadec-11-enoyl]amino]oxan-3-yl] dihydrogen phosphate
International Nonproprietary Names
INN number INN
8562 eritoran
Synonyms
B1287 | E5564
Database Links
CAS Registry No. 185955-34-4
ChEBI CHEBI:68609
ChEMBL Ligand CHEMBL501259
PubChem CID 6912404
RCSB PDB Ligand E55
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Wikipedia Eritoran
Comments
Eritoran is a synthetic analogue of lipid A, the bacterial LPS component. It is referred to as a Toll-like receptor 4 (TLR4) antagonist, but rather than direct interaction, eritoran binds to MD-2 and prevents formation of the MD-2.TLR4 protein complex. Thus, eritoran appears to antagonise LPS-induced TLR4 activation.
Eritoran has been investigated as a therapeutic for the management of sepsis, but failed to show sufficient clinical effect [1].