rotigaptide   Click here for help

GtoPdb Ligand ID: 9214

Synonyms: Dipeptide 9f [PMID 19175320] | GAP-134 | ZP-123
Compound class: Peptide
Comment: Rotigaptide is a hexapeptide developed originally by Wyeth, as an anti-arrhythmic agent. It promotes electrical coupling between ventricular myocytes by increasing gap junction conductance [1]. A recent study showed reduction in myocardial infarction size in a porcine model and protection from IRI-related endothelial dysfunction in man. Rotigaptide may thus have therapeutic potential in the treatment of myocardial infarction [2].

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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 OC1CC(N(C1)C(=O)C1CCCN1C(=O)C(Cc1ccc(cc1)O)NC(=O)C)C(=O)NCC(=O)NC(C(=O)NCC(=O)N)C
Isomeric SMILES O[C@H]1C[C@@H](N(C1)C(=O)[C@H]1CCCN1C(=O)[C@@H](Cc1ccc(cc1)O)NC(=O)C)C(=O)NCC(=O)N[C@@H](C(=O)NCC(=O)N)C
InChI InChI=1S/C28H39N7O9/c1-15(25(41)30-12-23(29)39)32-24(40)13-31-26(42)22-11-19(38)14-35(22)28(44)21-4-3-9-34(21)27(43)20(33-16(2)36)10-17-5-7-18(37)8-6-17/h5-8,15,19-22,37-38H,3-4,9-14H2,1-2H3,(H2,29,39)(H,30,41)(H,31,42)(H,32,40)(H,33,36)/t15-,19+,20-,21-,22-/m1/s1
InChI Key GFJRASPBQLDRRY-TWTQBQJDSA-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/)
Peptide Sequence Click here for help
Ac-D-Tyr-D-Pro-D-aHyp-Gly-D-Ala-Gly-NH2
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel