human GIP(3-30)NH2   Click here for help

GtoPdb Ligand ID: 8971

Compound class: Peptide
Comment: A naturally occurring truncated variant of gastric inhibitory polypeptide (GIP) which acts as a high affinity competitive GIP receptor antagonist [1].

An analogue of hGIP(3-30)NH2 (AT-7687; Antag Therapeutics) with amino acid substitutions and lipidation to optimise the peptide's PK/PD profile has been reported to improve weight loss and metabolic parameters in preclinical models [2] (n.b. full sequence not disclosed in this 2024 publication).
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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.

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 NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CCCCN)Cc1c[nH]c2c1cccc2)CC(=O)O)CC(=O)N)CCCCN)CCCCN)CCCCN)CCC(=O)N)C)CC(C)C)CC(C)C)Cc1c[nH]c2c1cccc2)CC(=O)N)C(C)C)Cc1ccccc1)CC(=O)O)CCC(=O)N)CCC(=O)N)Cc1nc[nH]c1)C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(C(O)C)NC(=O)CNC(=O)C(CCC(=O)O)N)Cc1ccccc1)CO)CC(=O)O)Cc1ccc(cc1)O)CO)C)CCSC)CC(=O)O
Isomeric SMILES CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](N)CCC(=O)O)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCCN)C(=O)O)C(C)C)[C@@H](C)CC
InChI InChI=1S/C189H285N49O55S/c1-17-97(10)153(238-183(286)139(92-240)232-170(273)126(76-105-53-55-109(242)56-54-105)220-178(281)137(85-151(258)259)228-182(285)138(91-239)233-187(290)155(99(12)19-3)237-181(284)128(75-104-42-24-21-25-43-104)229-188(291)156(102(15)241)234-146(249)90-204-159(262)112(195)57-64-147(250)251)185(288)208-101(14)158(261)211-122(65-71-294-16)166(269)226-134(82-148(252)253)176(279)214-118(51-33-38-69-193)167(270)236-154(98(11)18-2)186(289)230-131(79-108-88-201-93-206-108)173(276)216-120(59-62-141(197)244)164(267)215-121(60-63-142(198)245)165(268)225-135(83-149(254)255)177(280)221-127(74-103-40-22-20-23-41-103)180(283)235-152(96(8)9)184(287)231-133(81-144(200)247)175(278)222-130(78-107-87-203-114-47-29-27-45-111(107)114)172(275)219-125(73-95(6)7)169(272)218-124(72-94(4)5)168(271)207-100(13)157(260)210-119(58-61-140(196)243)163(266)212-115(48-30-35-66-190)160(263)205-89-145(248)209-116(49-31-36-67-191)161(264)213-117(50-32-37-68-192)162(265)224-132(80-143(199)246)174(277)227-136(84-150(256)257)179(282)223-129(77-106-86-202-113-46-28-26-44-110(106)113)171(274)217-123(189(292)293)52-34-39-70-194/h20-29,40-47,53-56,86-88,93-102,112,115-139,152-156,202-203,239-242H,17-19,30-39,48-52,57-85,89-92,190-195H2,1-16H3,(H2,196,243)(H2,197,244)(H2,198,245)(H2,199,246)(H2,200,247)(H,201,206)(H,204,262)(H,205,263)(H,207,271)(H,208,288)(H,209,248)(H,210,260)(H,211,261)(H,212,266)(H,213,264)(H,214,279)(H,215,267)(H,216,276)(H,217,274)(H,218,272)(H,219,275)(H,220,281)(H,221,280)(H,222,278)(H,223,282)(H,224,265)(H,225,268)(H,226,269)(H,227,277)(H,228,285)(H,229,291)(H,230,289)(H,231,287)(H,232,273)(H,233,290)(H,234,249)(H,235,283)(H,236,270)(H,237,284)(H,238,286)(H,250,251)(H,252,253)(H,254,255)(H,256,257)(H,258,259)(H,292,293)/t97-,98-,99-,100-,101-,102+,112-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,152-,153-,154-,155-,156-/m0/s1
InChI Key IOBVONZFFZDDEF-OTCKMHAFSA-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. Hansen LS, Sparre-Ulrich AH, Christensen M, Knop FK, Hartmann B, Holst JJ, Rosenkilde MM. (2016)
N-terminally and C-terminally truncated forms of glucose-dependent insulinotropic polypeptide are high-affinity competitive antagonists of the human GIP receptor.
Br J Pharmacol, 173 (5): 826-38. [PMID:26572091]
2. Jensen MH, Sanni SJ, Riber D, Holst JJ, Rosenkilde MM, Sparre-Ulrich AH. (2024)
AT-7687, a novel GIPR peptide antagonist, combined with a GLP-1 agonist, leads to enhanced weight loss and metabolic improvements in cynomolgus monkeys.
Mol Metab, 88: 102006. [PMID:39128651]