zyklophin   Click here for help

GtoPdb Ligand ID: 9193

Compound class: Peptide or derivative
Comment: Zyklophin is a cyclic analogue of dynorphin A-(1−11) with antagonist action selective for the κ opioid receptor. Structure, synthesis and function is described in [2], where it is peptide 2. The peptide is brain-penetrant, and has a relatively short duration of action compared to established small-molecule selective KOR antagonists such as nor-binaltorphimine [1].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 NCCCCC(C(=O)N)NC(=O)C1CCCN1C(=O)C(NC(=O)C1CNC(=O)CC(NC(=O)C(Cc2ccccc2)NC(=O)CNC(=O)CNC(=O)C(Cc2ccc(cc2)O)NCc2ccccc2)C(=O)NC(C(=O)NC(C(=O)N1)C(CC)C)CCCN=C(N)N)CCCN=C(N)N
Isomeric SMILES NCCCC[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H]1CNC(=O)C[C@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)CNC(=O)CNC(=O)[C@H](Cc2ccc(cc2)O)NCc2ccccc2)C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(CC)C)CCCN=C(N)N)CCCN=C(N)N
InChI InChI=1S/C65H96N20O13/c1-3-38(2)54-62(97)83-49(60(95)81-45(21-13-29-73-65(70)71)63(98)85-30-14-22-50(85)61(96)79-43(55(67)90)19-10-11-27-66)35-75-51(87)33-48(59(94)80-44(57(92)84-54)20-12-28-72-64(68)69)82-58(93)47(32-39-15-6-4-7-16-39)78-53(89)37-76-52(88)36-77-56(91)46(31-40-23-25-42(86)26-24-40)74-34-41-17-8-5-9-18-41/h4-9,15-18,23-26,38,43-50,54,74,86H,3,10-14,19-22,27-37,66H2,1-2H3,(H2,67,90)(H,75,87)(H,76,88)(H,77,91)(H,78,89)(H,79,96)(H,80,94)(H,81,95)(H,82,93)(H,83,97)(H,84,92)(H4,68,69,72)(H4,70,71,73)/t38?,43-,44-,45-,46-,47-,48-,49-,50-,54-/m0/s1
InChI Key UWLIKQFWZOPOAX-HRFULILYSA-N
References
1. Aldrich JV, Patkar KA, McLaughlin JP. (2009)
Zyklophin, a systemically active selective kappa opioid receptor peptide antagonist with short duration of action.
Proc Natl Acad Sci USA, 106 (43): 18396-401. [PMID:19841255]
2. Patkar KA, Yan X, Murray TF, Aldrich JV. (2005)
[Nalpha-benzylTyr1,cyclo(D-Asp5,Dap8)]- dynorphin A-(1-11)NH2 cyclized in the "address" domain is a novel kappa-opioid receptor antagonist.
J Med Chem, 48 (14): 4500-3. [PMID:15999987]