ecallantide   Click here for help

GtoPdb Ligand ID: 6955

Synonyms: DX-88 | FOV2302 | Kalbitor®
Approved drug Immunopharmacology Ligand
ecallantide is an approved drug (FDA (2009))
Compound class: Peptide
Comment: This 60 amino acid peptide drug is an inhibitor of human plasma kallikrein (KLKB1; P03952). The recombinant protein is produced in yeast (Pichia pastoris).The chemical structure shown here was generated using the SMILES from PubChem CID 44152182.
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 NCCCC[C@@H]1NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]4CCCN4C(=O)[C@H](Cc4cnc[nH]4)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)CNC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC3=O)CCC(=O)O)CCC(=O)O)Cc3ccccc3)[C@H](CC)C)Cc3ccc(cc3)O)C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=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)N[C@H](C(=O)N[C@H](C(=O)N2)CCC(=O)O)CCC(=O)O)CC(C)C)CO)CCC(=O)O)Cc2ccccc2)CCCNC(=N)N)CC(=O)N)CCC(=O)N)CC(=O)N)NC(=O)[C@H]2N(C(=O)CNC(=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](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCCCN)CCSC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)CCCNC(=N)N)[C@@H](O)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](CCC(=O)O)N)C)CCSC)Cc1cnc[nH]1)CO)Cc1ccccc1)C)Cc1ccccc1)CCCCN)C)CC(=O)O)CC(=O)O)CCC2)CCCNC(=N)N)C)C)Cc1c[nH]c2c1cccc2)[C@H](CC)C)[C@@H](O)C
Isomeric SMILES CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4CCC[C@H]4C(=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)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[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)NCC(=O)N4CCC[C@H]4C(=O)N3)CC(=O)O)CC(=O)O)C)CCCCN)Cc3ccccc3)C)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3cnc[nH]3)NC(=O)[C@H](CCSC)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)N)C(=O)N[C@@H]([C@H](C)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)O)C(=O)O)CCSC)CCCCN)CCCCN)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)[C@@H](NC(=O)CNC(=O)[C@@H](NC2=O)CCC(=O)O)CC(=O)N)CCC(=O)N)CC(=O)N)CCCNC(=N)N)Cc2ccccc2)CCC(=O)O)CO)CC(C)C)CCC(=O)O)CCC(=O)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1ccccc1)CCC(=O)O)CCC(=O)O)CCC(=O)N)CCCNC(=N)N)[C@H](C)O)Cc1ccccc1)[C@@H](C)CC)CC(=O)N)Cc1ccccc1)Cc1ccccc1)Cc1c[nH]c2ccccc12)CCCNC(=N)N)Cc1cnc[nH]1)C)C)CCCNC(=N)N)Cc1ccc(cc1)O
InChI Key VBGWSQKGUZHFPS-VGMMZINCSA-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. Cicardi M, Levy RJ, McNeil DL, Li HH, Sheffer AL, Campion M, Horn PT, Pullman WE. (2010)
Ecallantide for the treatment of acute attacks in hereditary angioedema.
N Engl J Med, 363 (6): 523-31. [PMID:20818887]