Compound ID | 689

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E5531

Class: Antimicrobial peptide

Agent Type: Natural product; Indirect acting;
Spectrum of activity: Gram-negative
Mechanism of action: Binds and neutralizes lipopolysaccharide and endotoxin to prevent the host's acute inflammatory response; endotoxin inhibitor; endotoxin antagonist
Description: An endotoxin antagonist; immunomodulator; Ackermann K, Kawata T, Christ A, et al. Role of liposaccharide binding protein (LBP) in liposaccharide binding and activation of murine macrophage cells; inhibition by E5531. 32nd-Intersci-Conf-Antimicrobial-Agents-Chemother 1992; 337.
Institute where first reported: Eisai Co. Ltd, Japan
Year first mentioned: 1992
Highest development stage: Phase 2
Development status: Inactive
Chemical structure(s):
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Molecular weight: 1455.81
Iso. SMILES: CCCCCCCCCCCC(=O)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC)OP(=O)(O)O)OCC[C@@H](CCCCCCC)OC(=O)CCC/C=C\CCCCCC)NC(=O)CC(=O)CCCCCCCCCCC)O)OCC[C@@H](CCCCCCC)O
InChI Key: GDODKYPBSZCPOO-XFMGTHRKSA-N
Can. SMILES: CCCCCCCCCCCC(=O)CC(=O)N[C@@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC)O2)OP(=O)(O)O)OCC[C@@H](CCCCCCC)OC(=O)CCC/C=C\CCCCCC)NC(=O)CC(=O)CCCCCCCCCCC)O[C@@H]1OP(=O)(O)O)O)OCC[C@@H](CCCCCCC)O
InChI: InChI=1S/C73H136N2O22P2/c1-7-12-17-22-25-28-31-36-40-45-58(77)53-63(79)74-66-70(90-51-49-57(76)44-39-34-20-15-10-4)68(82)61(94-73(66)97-99(86,87)88)56-92-72-67(75-64(80)54-59(78)46-41-37-32-29-26-23-18-13-8-2)71(69(96-98(83,84)85)62(95-72)55-89-6)91-52-50-60(47-42-35-21-16-11-5)93-65(81)48-43-38-33-30-27-24-19-14-9-3/h30,33,57,60-62,66-73,76,82H,7-29,31-32,34-56H2,1-6H3,(H,74,79)(H,75,80)(H2,83,84,85)(H2,86,87,88)/b33-30-/t57-,60-,61-,62-,66-,67-,68-,69-,70-,71-,72-,73-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6442269
Citations:
  • https://doi.org/10.1038/sj.bjp.0702596
  • https://doi.org/10.1126/science.7701344

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