BCY15291   Click here for help

GtoPdb Ligand ID: 12820

Compound class: Peptide or derivative
Comment: BCY15291 is a novel bicyclic peptide inhibitor of angiotensin-converting enzyme 2 (ACE2) [1]. It has improved potency and drug-like properties compared to DX600, and excellent selectivity for ACE2 over ACE. The crystal structure of human ACE2 in complex with BCY15291 has been resolved (PDB ID :8BYJ).
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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 interactive charts of activity data across species
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 CC[C@H](C)[C@H]1C(=O)N[C@@H](CC2=CNC=N2)C(=O)N[C@@H](CSCCC(=O)N3CN4CN(C3)C(=O)CCSC[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO[H])C(=O)N[C@@H](CC5=CNC=N5)C(=O)N[C@@H](CSCCC4=O)C(=O)N[C@@H](CO[H])C(=O)N[C@@H](CO[H])C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N6CCC[C@H]6C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1)NC(=O)[C@H](C)N[H])C(=O)N[C@@H](C)C(=O)N
Isomeric SMILES [H]N[C@@H](C)C(=O)N[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]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N)CSCCC(N4CN(CN(C4)C(CCSC2)=O)C(CCSC1)=O)=O)CC5=CNC=N5)CCCNC(N)=N)CO[H])CO[H])CC6=CNC=N6)CO[H])CCCNC(N)=N)C(C)C
InChI InChI=1S/C88H145N31O23S3/c1-11-47(8)69-85(141)106-56(30-51-32-96-40-100-51)76(132)112-61(80(136)101-49(10)70(90)126)36-143-24-18-65(123)116-41-117-43-118(42-116)67(125)20-26-145-38-63(111-71(127)48(9)89)82(138)114-68(46(6)7)84(140)103-52(15-12-21-97-87(91)92)72(128)108-58(33-120)78(134)105-55(29-50-31-95-39-99-50)75(131)113-62(37-144-25-19-66(117)124)81(137)110-60(35-122)79(135)109-59(34-121)77(133)104-54(27-44(2)3)74(130)107-57(28-45(4)5)86(142)119-23-14-17-64(119)83(139)102-53(73(129)115-69)16-13-22-98-88(93)94/h31-32,39-40,44-49,52-64,68-69,120-122H,11-30,33-38,41-43,89H2,1-10H3,(H2,90,126)(H,95,99)(H,96,100)(H,101,136)(H,102,139)(H,103,140)(H,104,133)(H,105,134)(H,106,141)(H,107,130)(H,108,128)(H,109,135)(H,110,137)(H,111,127)(H,112,132)(H,113,131)(H,114,138)(H,115,129)(H4,91,92,97)(H4,93,94,98)/t47-,48-,49-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,68-,69-/m0/s1
InChI Key ARJMONOCBCNTHY-GWVTULHFSA-N
References
1. Harman MAJ, Stanway SJ, Scott H, Demydchuk Y, Bezerra GA, Pellegrino S, Chen L, Brear P, Lulla A, Hyvönen M et al.. (2023)
Structure-Guided Chemical Optimization of Bicyclic Peptide (Bicycle) Inhibitors of Angiotensin-Converting Enzyme 2.
J Med Chem, 66 (14): 9881-9893. [PMID:37433017]