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larazotide   Click here for help

GtoPdb Ligand ID: 13724

Synonyms: AT-1001 | AT-2347 | AT1001 | AT2347
Compound class: Peptide
Comment: Larazotide (AT1001) is an eight amino acid oligopeptide. Its sequence is derived from the zonula occludens toxin that is secreted by Vibrio cholerae. In human tissues larazotide acts to restore the intercellular tight junction complex [1-2] and regulates epithelial and endothelial permeability by antagonising the effects of zonulin on the tight junction protein 1 (TJP1). Larazotide was proposed for potential therapeutic application in celiac disease where tight junctions and intestinal permeability are dysregulated [3-5].

larazotide is commercially available from our sponsors

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.

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/)

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Canonical SMILES CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)CN
Isomeric SMILES CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)CN
InChI InChI=1S/C32H55N9O10/c1-16(2)12-20(38-30(49)26(17(3)4)39-24(44)14-35-23(43)13-33)28(47)40-27(18(5)6)31(50)37-19(9-10-22(34)42)32(51)41-11-7-8-21(41)29(48)36-15-25(45)46/h16-21,26-27H,7-15,33H2,1-6H3,(H2,34,42)(H,35,43)(H,36,48)(H,37,50)(H,38,49)(H,39,44)(H,40,47)(H,45,46)/t19-,20-,21-,26-,27-/m0/s1
InChI Key ORFLZNAGUTZRLQ-ZMBVWFSWSA-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
IUPAC Name Click here for help
2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid
International Nonproprietary Names Click here for help
INN number INN
8951 larazotide
Synonyms Click here for help
AT-1001 | AT-2347 | AT1001 | AT2347
Database Links Click here for help
CAS Registry No. 258818-34-7 (source: WHO INN record)
ChEBI CHEBI:177799
ChEMBL Ligand CHEMBL2105646
DrugBank Ligand DB05645
GtoPdb PubChem SID 507750358
PubChem CID 9810532
Search Google for chemical match using the InChIKey ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
Search Google for chemicals with the same backbone ORFLZNAGUTZRLQ
Search PubMed clinical trials larazotide
Search PubMed titles larazotide
Search PubMed titles/abstracts larazotide
UniChem Compound Search for chemical match using the InChIKey ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
UniChem Connectivity Search for chemical match using the InChIKey ORFLZNAGUTZRLQ-ZMBVWFSWSA-N

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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.

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MedChemExpress
Larazotide (links to external site)
Cat. No. HY-106268