Compound ID | 690

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XMP-629

Synonym(s): XOMA-629

Class: Antimicrobial peptide

Agent Type: Natural product; Indirect acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Binds and neutralizes lipopolysaccharide and endotoxin to prevent the host's acute inflammatory response; endotoxin inhibitor; endotoxin antagonist
Target Pathogen: Active against Staphylococcus aureus and Pseudomonas aeruginosa
Description: A bactericidal permeability-increasing protein; a cationic alpha-helical peptide
Institute where first reported: XOMA Corp., US
Year first mentioned: 2001
Highest development stage: Phase 3
Development status: Inactive
Reason dropped: Failed to show efficacy
Chemical structure(s):
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Molecular weight: 1284.55
Iso. SMILES: C[C@H](C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC1=CC=CC2=CC=CC=C21)C(=O)O)NC(=O)[C@@H](CCC(=O)N)NC(=O)[C@@H](CC3=CC=CC4=CC=CC=C43)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CC5=CC=CC=C5)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CCCCN)N
InChI Key: YSPFONMJJGFGKC-KGEOJHTKSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CC2=CC=CC3=C2C=CC=C3)C(=O)N[C@H](CCC(=O)N)C(=O)N[C@H](C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC4=CC=CC5=C4C=CC=C5)C(=O)O)NC(=O)[C@@H](CCCCN)N
InChI: InChI=1S/C67H93N15O11/c1-40(2)36-53(79-59(85)49(70)28-11-13-33-68)63(89)80-54(37-42-18-5-4-6-19-42)64(90)77-51(30-17-35-74-67(72)73)61(87)81-55(38-45-24-15-22-43-20-7-9-26-47(43)45)65(91)78-52(31-32-57(71)83)60(86)75-41(3)58(84)76-50(29-12-14-34-69)62(88)82-56(66(92)93)39-46-25-16-23-44-21-8-10-27-48(44)46/h4-10,15-16,18-27,40-41,49-56H,11-14,17,28-39,68-70H2,1-3H3,(H2,71,83)(H,75,86)(H,76,84)(H,77,90)(H,78,91)(H,79,85)(H,80,89)(H,81,87)(H,82,88)(H,92,93)(H4,72,73,74)/t41-,49-,50-,51-,52-,53-,54-,55-,56-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9877039
Guide to Pharmacology: XMP-629
Citation: https://doi.org/10.1038/nrmicro2745

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