GNF4877   Click here for help

GtoPdb Ligand ID: 10688

Synonyms: GNF-4877
Compound class: Synthetic organic
Comment: GNF4877 is a dual DYRK1A/GSK3β inhibitor [3]. It was designed and reported by the Genomics Institute of the Novartis Research Foundation (GNF) as a strategy to increase β-cell mass and insulin levels, and to improve glycemic control as a novel therapy for type 1 diabetes. Although experiments conducted by the GNF team indicate that DYRK1A inhibition alone is sufficient to promote pancreatic β-cell proliferation, dual inhibition is synergistic. However, GSK3β inhibition may pose a cancer risk [1], so selective DYRK1A inhibitors have subsequently been designed (e.g. GNF2133) to ascertain the efficacy of DYRK1A inhibition alone [2].
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Ligand Activity Visualisation Charts

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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 CDK toolkit. 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 9
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 143.56
Molecular weight 494.21
XLogP 2.9
No. Lipinski's rules broken 0
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(Oc1ccc(c(c1)c1cnc(c(n1)C(=O)Nc1cnccc1N1CCC[C@H](C1)C(=O)O)N)F)C
Isomeric SMILES CC(Oc1ccc(c(c1)c1cnc(c(n1)C(=O)Nc1cnccc1N1CCC[C@H](C1)C(=O)O)N)F)C
InChI InChI=1S/C25H27FN6O4/c1-14(2)36-16-5-6-18(26)17(10-16)19-12-29-23(27)22(30-19)24(33)31-20-11-28-8-7-21(20)32-9-3-4-15(13-32)25(34)35/h5-8,10-12,14-15H,3-4,9,13H2,1-2H3,(H2,27,29)(H,31,33)(H,34,35)/t15-/m1/s1
InChI Key UZIATSFXNVOVFE-OAHLLOKOSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3R)-1-[3-[[3-amino-6-(2-fluoro-5-propan-2-yloxyphenyl)pyrazine-2-carbonyl]amino]pyridin-4-yl]piperidine-3-carboxylic acid
Synonyms Click here for help
GNF-4877
Database Links Click here for help
CAS Registry No. 2041073-22-5 (source: PubChem)
GtoPdb PubChem SID 404859135
PubChem CID 139600315
Search Google for chemical match using the InChIKey UZIATSFXNVOVFE-OAHLLOKOSA-N
Search Google for chemicals with the same backbone UZIATSFXNVOVFE
UniChem Compound Search for chemical match using the InChIKey UZIATSFXNVOVFE-OAHLLOKOSA-N
UniChem Connectivity Search for chemical match using the InChIKey UZIATSFXNVOVFE-OAHLLOKOSA-N