peptide 14 [PMID: 36580549]   Click here for help

GtoPdb Ligand ID: 12333

Compound class: Peptide or derivative
Comment: This is a synthetic macrocyclic peptide that was designed to disrupt the protein-protein interaction between postsynaptic density protein-95 (PSD-95; gene symbol DLG4) and neuronal nitric oxide synthase (nNOS) [1], as a mechanism to disrupt the excitotoxic signaling and cell death that's induced (in acute ischaemia) by formation of the tri-protein complex of glutamate ionotropic receptor NMDA type subunit 2B (GRIN2B; GluN2B or NR2B), PSD-95 and nNOS. Structurally it mimics the β-hairpin motif of nNOS that forms the interaction with the PDZ2 domain of PSD-95.
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 NCCCC[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]2N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)[C@H](O)C)[C@H](CC)C)CCCNC(=N)N)C(C)C)[C@H](O)C)CCC(=O)N)CCC2)CCC(=O)N)[C@H](O)C)Cc1cnc[nH]1)[C@H](O)C)[C@H](O)C)[C@H](O)C)[C@H](O)C
Isomeric SMILES O=C1N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@H](CC)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N2CCC[C@@H]2C(=O)NCC(=O)N[C@H](C(=O)N[C@H]1[C@@H](C)O)CCC(=O)N)CC(=O)O)C)Cc1ccccc1)Cc1cnc[nH]1
InChI InChI=1S/C108H173N31O36/c1-15-50(6)79-99(167)123-62(27-21-37-115-108(112)113)89(157)130-78(49(4)5)98(166)136-82(54(10)142)101(169)124-65(31-34-73(111)148)106(174)138-38-22-28-70(138)96(164)117-45-74(149)120-63(30-33-72(110)147)91(159)132-81(53(9)141)102(170)128-68(42-60-44-114-47-118-60)94(162)126-66(40-48(2)3)93(161)121-64(32-35-76(151)152)92(160)134-85(57(13)145)105(173)137-83(55(11)143)103(171)127-67(41-59-24-17-16-18-25-59)95(163)135-80(52(8)140)100(168)119-51(7)87(155)125-69(43-77(153)154)88(156)116-46-75(150)129-86(58(14)146)107(175)139-39-23-29-71(139)97(165)122-61(26-19-20-36-109)90(158)133-84(56(12)144)104(172)131-79/h16-18,24-25,44,47-58,61-71,78-86,140-146H,15,19-23,26-43,45-46,109H2,1-14H3,(H2,110,147)(H2,111,148)(H,114,118)(H,116,156)(H,117,164)(H,119,168)(H,120,149)(H,121,161)(H,122,165)(H,123,167)(H,124,169)(H,125,155)(H,126,162)(H,127,171)(H,128,170)(H,129,150)(H,130,157)(H,131,172)(H,132,159)(H,133,158)(H,134,160)(H,135,163)(H,136,166)(H,137,173)(H,151,152)(H,153,154)(H4,112,113,115)/t50-,51-,52+,53+,54+,55+,56+,57+,58+,61-,62-,63-,64-,65-,66-,67-,68-,69-,70+,71-,78-,79-,80-,81-,82-,83-,84-,85-,86-/m0/s1
InChI Key XRFRKHKXUPWIIL-HAOGKZSMSA-N
Peptide Sequence Click here for help
Cyclo(105THLETTFTADGTPKTIRVTQ124pG(Qα))
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel