repinatrabit   Click here for help

GtoPdb Ligand ID: 12899

Synonyms: JNT-517 | JNT517
Compound class: Synthetic organic
Comment: JNT-517 (Jnana Therapeutics) is an oral, allosteric inhibitor of SCL6A19-mediated phenylalanine reabsorption in the kidney. It is in clinical development for potential to treat phenylketonuria, an inherited metabolic disorder caused by phenylalanine hydroxylase (PAH) deficiency. The chemical structure shown here was revealed during the First Time Disclosures session at the ACS meeting in September 2023, and we picked it up from Drug Hunter. Jnana Therapeutics have a patent that claims small molecule SCL6A19 inhibitors (WO2023122267A2), but this structure doesn't appear in that patent [1]. The chemical structure for JNT-517 was matched to that for the INN repinatrabit from WHO proposed INN list 131 (August 2024).

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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 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 7
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 87.9
Molecular weight 418.39
XLogP 1.41
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 C1C[C@H](CN(C1)C(=O)N)N(C2CC2)C(=O)NCC3=CC=C(C=C3F)OC(F)(F)F
Isomeric SMILES NC(=O)N1CCC[C@H](C1)N(C2CC2)C(=O)NCC3=CC=C(OC(F)(F)F)C=C3F
InChI InChI=1S/C18H22F4N4O3/c19-15-8-14(29-18(20,21)22)6-3-11(15)9-24-17(28)26(12-4-5-12)13-2-1-7-25(10-13)16(23)27/h3,6,8,12-13H,1-2,4-5,7,9-10H2,(H2,23,27)(H,24,28)/t13-/m1/s1
InChI Key FNRHWODWSBDOOY-CYBMUJFWSA-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/)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel