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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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
Search Google for chemical match using the InChIKey BPSMYQFMCXXNPC-MFCPCZTFSA-N
Search Google for chemicals with the same backbone BPSMYQFMCXXNPC
Search PubMed clinical trials eritoran
Search PubMed titles eritoran
Search PubMed titles/abstracts eritoran
UniChem Compound Search for chemical match using the InChIKey BPSMYQFMCXXNPC-MFCPCZTFSA-N
UniChem Connectivity Search for chemical match using the InChIKey BPSMYQFMCXXNPC-MFCPCZTFSA-N
Wikipedia Eritoran