iseganan   Click here for help

GtoPdb Ligand ID: 10822

Synonyms: IB-367 | IB-367-03
Compound class: Peptide or derivative
Comment: Iseganan is a synthetic protegrin peptide with bactericidal, fungicidal and antiendotoxin activities [1-2].
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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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.

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Canonical SMILES O=C(CNC(=O)[C@H](CCCNC(=N)N)N)NCC(=O)N[C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N2)Cc1ccccc1)CCCNC(=N)N)C(C)C)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N)CCCNC(=N)N)C(C)C)CC(C)C
Isomeric SMILES O=C(CNC(=O)[C@H](CCCNC(=N)N)N)NCC(=O)N[C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N2)Cc1ccccc1)CCCNC(=N)N)C(C)C)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N)CCCNC(=N)N)C(C)C)CC(C)C
InChI InChI=1S/C78H126N30O18S4/c1-39(2)28-49(99-57(111)32-93-56(110)31-94-63(115)45(79)16-10-24-89-75(81)82)66(118)103-53-36-128-130-38-55(72(124)107-60(40(3)4)73(125)96-34-58(112)97-46(62(80)114)17-11-25-90-76(83)84)106-74(126)61(41(5)6)108-71(123)54-37-129-127-35-52(104-68(120)51(102-70(53)122)30-43-20-22-44(109)23-21-43)69(121)100-47(18-12-26-91-77(85)86)64(116)95-33-59(113)98-48(19-13-27-92-78(87)88)65(117)101-50(67(119)105-54)29-42-14-8-7-9-15-42/h7-9,14-15,20-23,39-41,45-55,60-61,109H,10-13,16-19,24-38,79H2,1-6H3,(H2,80,114)(H,93,110)(H,94,115)(H,95,116)(H,96,125)(H,97,112)(H,98,113)(H,99,111)(H,100,121)(H,101,117)(H,102,122)(H,103,118)(H,104,120)(H,105,119)(H,106,126)(H,107,124)(H,108,123)(H4,81,82,89)(H4,83,84,90)(H4,85,86,91)(H4,87,88,92)/t45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,60-,61-/m0/s1
InChI Key GUCYBPFJNGVFEB-XELKFLSISA-N
References
1. Giacometti A, Cirioni O, Ghiselli R, Mocchegiani F, D'Amato G, Del Prete MS, Orlando F, Kamysz W, Lukasiak J, Saba V et al.. (2003)
Administration of protegrin peptide IB-367 to prevent endotoxin induced mortality in bile duct ligated rats.
Gut, 52 (6): 874-8. [PMID:12740345]
2. Mosca DA, Hurst MA, So W, Viajar BS, Fujii CA, Falla TJ. (2000)
IB-367, a protegrin peptide with in vitro and in vivo activities against the microflora associated with oral mucositis.
Antimicrob Agents Chemother, 44 (7): 1803-8. [PMID:10858334]