zyklophin   Click here for help

GtoPdb Ligand ID: 9193

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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2D Structure
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SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Peptide or derivative
Database Links Click here for help
BindingDB Ligand 50299408
ChEMBL Ligand CHEMBL574568
GtoPdb PubChem SID 315661272
PubChem CID 45483651
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Wikipedia Zyklophin