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BMS-986238   Click here for help

GtoPdb Ligand ID: 13877

Synonyms: BMS 986238 | BMS986238
Immunopharmacology Ligand
Compound class: Peptide
Comment: BMS-986238 is a macrocyclic peptide that inhibits programmed death-ligand 1 (PD-L1) [3]. It was designed as an alternative to anti-PD-L1 monoclonal antibodies and is a preclinical lead. Related structures are claimed in Bristol-Myers Squibb's patent WO2016077518A1 [1] with thioether peptide synthetic procedures described in [2].
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 CCCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSCC(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N(C)[C@@H](C)C(=O)N[C@@H](CC(=O)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CN)C(=O)N[C@@H](CC(C)C)C(=O)N4C[C@@H](C[C@H]4C(=O)N[C@@H](CC5=CNC6=C5C=CC=C6)C(=O)N[C@@H](CCN)C(=O)N[C@@H](CC7=CN(CC(=O)O)C8=C7C=CC=C8)C(=O)N(C)[C@@H](CCCC)C(=O)N1C)O)C(=O)NCC(=O)N[C@@H](CC9=CN(CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CC[C@@H](C(=O)O)NC(=O)CCCCCCCCCCCCCCCCC(=O)O)N=N9)C(=O)O
Isomeric SMILES CCCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CSCC(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N3C[C@@H](C[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N1C)CCCC)C)CC4=CN(C5=CC=CC=C54)CC(=O)O)CCN)CC6=CNC7=CC=CC=C76)O)CC(C)C)CN)CC(=O)N)C)C)CC8=CC=C(C=C8)O)C(=O)NCC(=O)N[C@@H](CC9=CN(N=N9)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CC[C@@H](C(=O)O)NC(=O)CCCCCCCCCCCCCCCCC(=O)O)C(=O)O)CC(C)C
InChI InChI=1S/C143H224N26O40S/c1-11-13-37-117-134(187)154-107(76-93(3)4)131(184)160-115(129(182)149-86-124(175)152-113(143(197)198)81-99-88-167(162-161-99)53-55-200-57-59-202-61-63-204-65-67-206-69-71-208-73-75-209-74-72-207-70-68-205-66-64-203-62-60-201-58-56-199-54-51-147-122(173)48-47-106(142(195)196)150-123(174)41-27-25-23-21-19-17-15-16-18-20-22-24-26-28-42-126(177)178)91-210-92-125(176)151-110(78-96-43-45-100(170)46-44-96)137(190)163(8)95(7)128(181)156-112(83-121(146)172)139(192)168-52-33-40-118(168)135(188)159-114(84-145)133(186)157-109(77-94(5)6)140(193)169-89-101(171)82-120(169)136(189)155-108(79-97-85-148-104-36-31-29-34-102(97)104)132(185)153-105(49-50-144)130(183)158-111(138(191)165(10)119(38-14-12-2)141(194)164(117)9)80-98-87-166(90-127(179)180)116-39-32-30-35-103(98)116/h29-32,34-36,39,43-46,85,87-88,93-95,101,105-115,117-120,148,170-171H,11-28,33,37-38,40-42,47-84,86,89-92,144-145H2,1-10H3,(H2,146,172)(H,147,173)(H,149,182)(H,150,174)(H,151,176)(H,152,175)(H,153,185)(H,154,187)(H,155,189)(H,156,181)(H,157,186)(H,158,183)(H,159,188)(H,160,184)(H,177,178)(H,179,180)(H,195,196)(H,197,198)/t95-,101+,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,117-,118-,119-,120-/m0/s1
InChI Key IQRNUGWYTJONBD-LJOMSQDUSA-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. Gillman KW, Goodrich J, Boy KM, Zhang Y, Mapelli C, Poss MA, Sun LQ, Zhao Q, Mull E, Gillis EP, Scola PM, Langley DR. (2016)
Macrocyclic peptides useful as immunomodulators.
Patent number: WO2016077518A1. Assignee: Bristol-Myers Squibb Company. Priority date: 12/11/2015. Publication date: 19/05/2016.
2. Kempson J, Zhao R, Pawluczyk J, Wang B, Zhang H, Hou X, Allen MP, Wu DR, Li P, Yip S et al.. (2024)
Challenges with the Synthesis of a Macrocyclic Thioether Peptide: From Milligram to Multigram Using Solid Phase Peptide Synthesis (SPPS).
J Org Chem, 89 (10): 6639-6650. [PMID:38651358]
3. Scola PM. 
Discovery of BMS-986238, a second-generation macrocyclic peptide inhibitor of programmed death-ligand 1 (PD-L1).
Accessed on 05/05/2025. Modified on 05/05/2025. ACS, https://acs.digitellinc.com/p/s/discovery-of-bms-986238-a-second-generation-macrocyclic-peptide-inhibitor-of-programmed-death-ligand-1-pd-l1-620196