nerinetide   Click here for help

GtoPdb Ligand ID: 12332

Synonyms: NA-1 | Tat-NR2B9c
Compound class: Peptide
Comment: Nerinetide (NA-1) is a peptide that was designed to target the PDZ domain of the PSD-95 protein (gene symbol DLG4) [1] to prevent its interaction with N-methyl-D-aspartate receptors (NMDARs) and neuronal nitric oxide synthase (nNOS) and block assembly of the tri-peptide complex that is a therapeutic target for the treatment of acute ischemic stroke [2-3]. Structurally, nerinetide is a 20 amino acid linear peptide that comprises nine residues derived from the COOH-terminal of the NR2B NMDAR (GluN2B; GRIN2B; that directly interacts with PSD-95's PDZ2 domain) fused to 11 amino acid cell-membrane transduction domain of the HIV-1 Tat protein (Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg; to create a cell permeable peptide). The NMDAR/nNOS/PSD-95 complex mediates neurotoxic signaling, and disruption of this function provides a neuroprotective effect that ameliorates ischemic brain damage, without inducing the negative consequences that can arise through NMDAR blockade.

nerinetide is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)C(C)C)CC(=O)O)CO)CCC(=O)O)[C@H](CC)C)CO)CO)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)CCCNC(=N)N)CCCCN)CCCCN)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
InChI InChI=1S/C105H188N42O30/c1-7-55(6)80(98(175)140-69(34-36-77(154)155)92(169)143-72(50-148)95(172)142-71(48-78(156)157)94(171)146-79(54(4)5)99(176)177)147-97(174)74(52-150)145-96(173)73(51-149)144-93(170)70(46-53(2)3)141-90(167)62(22-10-13-39-108)133-85(162)63(24-15-41-124-101(113)114)135-87(164)65(26-17-43-126-103(117)118)136-88(165)66(27-18-44-127-104(119)120)138-91(168)68(33-35-75(110)152)139-89(166)67(28-19-45-128-105(121)122)137-86(163)64(25-16-42-125-102(115)116)134-84(161)61(21-9-12-38-107)132-83(160)60(20-8-11-37-106)131-82(159)59(23-14-40-123-100(111)112)130-76(153)49-129-81(158)58(109)47-56-29-31-57(151)32-30-56/h29-32,53-55,58-74,79-80,148-151H,7-28,33-52,106-109H2,1-6H3,(H2,110,152)(H,129,158)(H,130,153)(H,131,159)(H,132,160)(H,133,162)(H,134,161)(H,135,164)(H,136,165)(H,137,163)(H,138,168)(H,139,166)(H,140,175)(H,141,167)(H,142,172)(H,143,169)(H,144,170)(H,145,173)(H,146,171)(H,147,174)(H,154,155)(H,156,157)(H,176,177)(H4,111,112,123)(H4,113,114,124)(H4,115,116,125)(H4,117,118,126)(H4,119,120,127)(H4,121,122,128)/t55-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,79-,80-/m0/s1
InChI Key XWQVQFBTSBCKLI-FKXNDIMNSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Peptide
International Nonproprietary Names Click here for help
INN number INN
10857 nerinetide
Synonyms Click here for help
NA-1 | Tat-NR2B9c
Database Links Click here for help
CAS Registry No. 500992-11-0 (source: WHO INN record)
GtoPdb PubChem SID 479821123
PubChem CID 44568939
Search Google for chemical match using the InChIKey XWQVQFBTSBCKLI-FKXNDIMNSA-N
Search Google for chemicals with the same backbone XWQVQFBTSBCKLI
Search PubMed clinical trials nerinetide
Search PubMed titles nerinetide
Search PubMed titles/abstracts nerinetide
UniChem Compound Search for chemical match using the InChIKey XWQVQFBTSBCKLI-FKXNDIMNSA-N
UniChem Connectivity Search for chemical match using the InChIKey XWQVQFBTSBCKLI-FKXNDIMNSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
Tat-NR2B9c (links to external site)
Cat. No. HY-P0117