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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/)
Peptide Sequence Click here for help
Ac-Tyr-{NMe-Ala}-Asn-Pro-Dap-Leu-Hyp-Trp-Dab-Trp{CH2COOH}-{NMe-Nle}-(NMe-Nle)-Leu-Cys-Gly-DPra(azido-PEG11-γGlu-C18 diacid)
Chemical Modification
Thioether bridge between Tyr1 and Cys14
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel