lepirudin   Click here for help

GtoPdb Ligand ID: 6469

Synonyms: 1-L-leucine-2-L-threonine-63-desulfohirudin | Refludan®
Approved drug
lepirudin is an approved drug (FDA (1998))
Compound class: Peptide
Comment: Discontinued (not withdrawn). The drug is a recombinant form of hirudin, the salivary anticoagulant found in leeches (see UniProt P01050), but has two amino acid modifications; substitution of Leu1 for Ile and no sulfate group on Tyr63. The PubChem entry linked to above represents the chemical structure of Lepirudin.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View more information in the IUPHAR Pharmacology Education Project: lepirudin

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](C(=O)N1CCC[C@H]1C(=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)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)N1CCC[C@H]1C(=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)CCC(=O)N)CC(C)C)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)[C@H](CC)C)CCC(=O)O)CCC(=O)O)Cc1ccccc1)CC(=O)O)CC(=O)O)CC(=O)N)Cc1nc[nH]c1)CO)CCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CSSC[C@@H]2NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC2=O)CCC(=O)N)CC(=O)N)CCCCN)C(=O)N[C@@H]([C@H](CC)C)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCC(=O)N)CC(=O)N)CCCCN)CCC(=O)O)CC(=O)O)CO)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](CC(C)C)N)Cc2ccc(cc2)O)CC(=O)O)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(C)C)CC(=O)N)CCC(=O)N)CO)CC(C)C)C(C)C)CCC(=O)O
Isomeric SMILES NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=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)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)N1CCC[C@H]1C(=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)CCC(=O)N)CC(C)C)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)[C@H](CC)C)CCC(=O)O)CCC(=O)O)Cc1ccccc1)CC(=O)O)CC(=O)O)CC(=O)N)Cc1nc[nH]c1)CO)CCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CSSC[C@@H]2NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC2=O)CCC(=O)N)CC(=O)N)CCCCN)C(=O)N[C@@H]([C@H](CC)C)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCC(=O)N)CC(=O)N)CCCCN)CCC(=O)O)CC(=O)O)CO)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](CC(C)C)N)Cc2ccc(cc2)O)CC(=O)O)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(C)C)CC(=O)N)CCC(=O)N)CO)CC(C)C)C(C)C)CCC(=O)O
InChI Key FIBJDTSHOUXTKV-BRHMIFOHSA-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
LVYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ
H-Leu-Thr-Tyr-Thr-Asp-Cys(1)-Thr-Glu-Ser-Gly-Gln-Asn-Leu-Cys(1)-Leu-Cys(2)-Glu-Gly-Ser-Asn-Val-Cys(3)-Gly-Gln-Gly-Asn-Lys-Cys(2)-Ile-Leu-Gly-Ser-Asp-Gly-Glu-Lys-Asn-Gln-Cys(3)-Val-Thr-Gly-Glu-Gly-Thr-Pro-Lys-Pro-Gln-Ser-His-Asn-Asp-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-Gln-OH
HELM Notation Click here for help
PEPTIDE1{L.T.Y.T.D.C.T.E.S.G.Q.N.L.C.L.C.E.G.S.N.V.C.G.Q.G.N.K.C.I.L.G.S.D.G.E.K.N.Q.C.V.T.G.E.G.T.P.K.P.Q.S.H.N.D.G.D.F.E.E.I.P.E.E.Y.L.Q}$PEPTIDE1,PEPTIDE1,6:R3-14:R3|PEPTIDE1,PEPTIDE1,16:R3-28:R3|PEPTIDE1,PEPTIDE1,22:R3-39:R3$$$
Post-translational Modification
I1L at the N-terminal and absence of a sulfate group at Y63.
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download

Molecular structure representations generated using Open Babel