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GRA2   Click here for help

GtoPdb Ligand ID: 13991

Compound class: Synthetic organic
Comment: GRA2 is reported to act as an inverse agonist of GPR21 [1].
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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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 47.56
Molecular weight 369.41
XLogP 3.19
No. Lipinski's rules broken 0

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/)
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 C1=CC=C(C=C1)OC2=C(C=CC=C2)NC(=O)COC3=CC=CC4=C3C=CC=C4
Isomeric SMILES C1=CC=C(C=C1)OC2=CC=CC=C2NC(=O)COC3=CC=CC4=CC=CC=C43
InChI InChI=1S/C24H19NO3/c26-24(17-27-22-16-8-10-18-9-4-5-13-20(18)22)25-21-14-6-7-15-23(21)28-19-11-2-1-3-12-19/h1-16H,17H2,(H,25,26)
InChI Key DHEDDHQEGVSGOT-UHFFFAOYSA-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. Bordano V, Kinsella GK, Cannito S, Dianzani C, Gigliotti CL, Stephens JC, Monge C, Bocca C, Rosa AC, Miglio G et al.. (2022)
G protein-coupled receptor 21 in macrophages: An in vitro study.
Eur J Pharmacol, 926: 175018. [PMID:35537492]
2. Gardner J, Wu S, Ling L, Danao J, Li Y, Yeh WC, Tian H, Baribault H. (2012)
G-protein-coupled receptor GPR21 knockout mice display improved glucose tolerance and increased insulin response.
Biochem Biophys Res Commun, 418 (1): 1-5. [PMID:22155242]
3. Lin X, Chen B, Wu Y, Han Y, Qi A, Wang J, Yang Z, Wei X, Zhao T, Wu L et al.. (2023)
Cryo-EM structures of orphan GPR21 signaling complexes.
Nat Commun, 14 (1): 216. [PMID:36639690]
4. Osborn O, Oh da Y, McNelis J, Sanchez-Alavez M, Talukdar S, Lu M, Li P, Thiede L, Morinaga H, Kim JJ et al.. (2012)
G protein-coupled receptor 21 deletion improves insulin sensitivity in diet-induced obese mice.
J Clin Invest, 122 (7): 2444-53. [PMID:22653059]
5. Wang J, Pan Z, Baribault H, Chui D, Gundel C, Véniant M. (2016)
GPR21 KO mice demonstrate no resistance to high fat diet induced obesity or improved glucose tolerance.
F1000Res, 5: 136. [PMID:27081476]