Compound ID | 689

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E 5531

Class: Antimicrobial peptide

Spectrum of activity: Gram-negative
Details of activity: The immune system is throught to over react to LPS (liposacharides) of the invading bacteria resulting in the overexpression of cytokines and vasoactive nitric oxide which damages tissues. This is thought to result in sepsis. E5531 competes with LBP (liposaccharide binding protein) preventing binding to LPS receptors and hence protecting the host. E5531 is a potent inhibitor of LPS/LBP mediated cellular activation.
Description: Ackermann K, Kawata T, Christ A, et al. Role of liposaccharide binding protein (LBP) in liposaccharide binding and activation of murine macrophase 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 developmental phase: 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
Citation: https://bpspubs.onlinelibrary.wiley.com/doi/10.1038/sj.bjp.0702596

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