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].
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 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/)
References
1. Gopalakrishnan S, Durai M, Kitchens K, Tamiz AP, Somerville R, Ginski M, Paterson BM, Murray JA, Verdu EF, Alkan SS et al.. (2012)
Larazotide acetate regulates epithelial tight junctions in vitro and in vivo.
Peptides, 35 (1): 86-94. [PMID:22401908]
2. Gopalakrishnan S, Tripathi A, Tamiz AP, Alkan SS, Pandey NB. (2012)
Larazotide acetate promotes tight junction assembly in epithelial cells.
Peptides, 35 (1): 95-101. [PMID:22401910]
3. Hoilat GJ, Altowairqi AK, Ayas MF, Alhaddab NT, Alnujaidi RA, Alharbi HA, Alyahyawi N, Kamal A, Alhabeeb H, Albazee E et al.. (2022)
Larazotide acetate for treatment of celiac disease: A systematic review and meta-analysis of randomized controlled trials.
Clin Res Hepatol Gastroenterol, 46 (1): 101782. [PMID:34339872]
4. Khaleghi S, Ju JM, Lamba A, Murray JA. (2016)
The potential utility of tight junction regulation in celiac disease: focus on larazotide acetate.
Therap Adv Gastroenterol, 9 (1): 37-49. [PMID:26770266]
5. McCarville JL, Caminero A, Verdu EF. (2015)
Pharmacological approaches in celiac disease.
Curr Opin Pharmacol, 25: 7-12. [PMID:26414923]