eritoran   Click here for help

GtoPdb Ligand ID: 4919

Synonyms: B1287 | E5564
PDB Ligand
Compound class: Synthetic organic
Comment: 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].
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCCCOC1C(O)C(COC2OC(COC)C(C(C2NC(=O)CCCCCCCCCC=CCCCCCC)OCCC(CCCCCCC)OC)OP(=O)(O)O)OC(C1NC(=O)CC(=O)CCCCCCCCCCC)OP(=O)(O)O
Isomeric SMILES CCCCCCCCCCO[C@H]1[C@H](O)[C@@H](CO[C@@H]2O[C@H](COC)[C@H]([C@@H]([C@H]2NC(=O)CCCCCCCCC/C=C\CCCCCC)OCC[C@@H](CCCCCCC)OC)OP(=O)(O)O)O[C@@H]([C@@H]1NC(=O)CC(=O)CCCCCCCCCCC)OP(=O)(O)O
InChI InChI=1S/C66H126N2O19P2/c1-7-11-15-19-22-25-26-27-28-29-30-32-34-38-42-46-57(70)67-60-64(82-49-47-54(80-6)45-41-36-18-14-10-4)62(86-88(73,74)75)56(51-79-5)85-65(60)83-52-55-61(72)63(81-48-43-39-35-24-21-17-13-9-3)59(66(84-55)87-89(76,77)78)68-58(71)50-53(69)44-40-37-33-31-23-20-16-12-8-2/h25-26,54-56,59-66,72H,7-24,27-52H2,1-6H3,(H,67,70)(H,68,71)(H2,73,74,75)(H2,76,77,78)/b26-25-/t54-,55-,56-,59-,60-,61-,62-,63-,64-,65-,66-/m1/s1
InChI Key BPSMYQFMCXXNPC-MFCPCZTFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(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 Click here for help
INN number INN
8562 eritoran
Synonyms Click here for help
B1287 | E5564
Database Links Click here for help
CAS Registry No. 185955-34-4
ChEBI CHEBI:68609
ChEMBL Ligand CHEMBL501259
GtoPdb PubChem SID 178101618
PubChem CID 6912404
RCSB PDB Ligand E55
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Wikipedia Eritoran