endothelin-1   Click here for help

GtoPdb Ligand ID: 989

Abbreviated name: ET-1
Compound class: Endogenous peptide in human, mouse or rat
Comment: Endothelin-1 (ET-1) is a 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production (for reviews see [2] and [3] ). As peptides defined by SMILES strings PubChem contains a number of alternative CIDs either with the name "Endothelin-1" and/or Mw 2491.914. Our choice of PubChem CID 16212950 reflects the majority of sources submitting substance structures and assay data.
COVID-19: The level of ET-1 in plasma from COVID-19 patients positively correlates with clinical severity of illness [1]. This finding suggests that endothelin receptor antagonists may provide a therapeutic option for some COVID-19 patients.
Species: Human, Mouse, Rat
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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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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.

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Canonical SMILES NCCCCC1NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(NC(=O)C2CSSCC(NC(=O)C(NC1=O)CCC(=O)O)C(=O)NC(C(C)C)C(=O)NC(Cc1ccc(cc1)O)C(=O)NC(Cc1ccccc1)C(=O)NC(CSSCC(C(=O)NC(C(=O)N2)CO)N)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1c[nH]c2c1cccc2)C(CC)C)C(CC)C)CC(=O)O)CC(C)C)Cc1cnc[nH]1)CO
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@@H](NC1=O)CCC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)CO)N)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)O)Cc1c[nH]c2c1cccc2)[C@H](CC)C)[C@H](CC)C)CC(=O)O)CC(C)C)Cc1cnc[nH]1)CO
InChI InChI=1S/C109H159N25O32S5/c1-12-56(9)87(107(163)125-76(109(165)166)39-60-43-113-65-24-18-17-23-63(60)65)134-108(164)88(57(10)13-2)133-99(155)75(42-85(143)144)123-94(150)70(36-54(5)6)118-97(153)73(40-61-44-112-52-114-61)121-103(159)80-49-169-168-48-64(111)89(145)126-77(45-135)102(158)131-81-50-170-171-51-82(105(161)132-86(55(7)8)106(162)124-72(38-59-26-28-62(138)29-27-59)95(151)120-71(96(152)130-80)37-58-21-15-14-16-22-58)129-91(147)67(30-31-83(139)140)116-90(146)66(25-19-20-33-110)115-98(154)74(41-84(141)142)122-92(148)68(32-34-167-11)117-93(149)69(35-53(3)4)119-100(156)78(46-136)127-101(157)79(47-137)128-104(81)160/h14-18,21-24,26-29,43-44,52-57,64,66-82,86-88,113,135-138H,12-13,19-20,25,30-42,45-51,110-111H2,1-11H3,(H,112,114)(H,115,154)(H,116,146)(H,117,149)(H,118,153)(H,119,156)(H,120,151)(H,121,159)(H,122,148)(H,123,150)(H,124,162)(H,125,163)(H,126,145)(H,127,157)(H,128,160)(H,129,147)(H,130,152)(H,131,158)(H,132,161)(H,133,155)(H,134,164)(H,139,140)(H,141,142)(H,143,144)(H,165,166)/t56-,57-,64-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,86-,87-,88-/m0/s1
InChI Key ZUBDGKVDJUIMQQ-ZTNLKOGPSA-N
Natural/Endogenous Targets
Target
ETA receptor
ETB receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Endothelin-converting enzyme 1
Endothelin-converting enzyme 2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ETA receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.8 – 8.5 pIC50 - 4
⤷ pIC50 7.8 – 8.5 [4]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at ETA receptor endothelin-1 (EDN1, P05305) = endothelin-2 (EDN2, P20800) > endothelin-3 (EDN3, P14138) 4
Potency order of endogenous ligands at ETB receptor endothelin-1 (EDN1, P05305) = endothelin-2 (EDN2, P20800), endothelin-3 (EDN3, P14138) 5
Endogenous substrates at Endothelin-converting enzyme 1 endothelin-1 (EDN1, P05305), endothelin-2 (EDN2, P20800), endothelin-3 (EDN3, P14138)
Endogenous substrates at Endothelin-converting enzyme 2 endothelin-1 (EDN1, P05305), endothelin-2 (EDN2, P20800), endothelin-3 (EDN3, P14138)
Ligand mentioned in the following text fields
Endothelin receptors overview
Endothelin receptors comments