TNG908   Click here for help

GtoPdb Ligand ID: 13320

Synonyms: TNG-908
PDB Ligand
Compound class: Synthetic organic
Comment: TNG908 is a small molecule competitive, reversible inhibitor of protein arginine methyltransferase 5 (PRMT5) with selectivity for PRMT5 that is in complex with methylthioadenosine (MTA) [1], a product of the enzyme methylthioadenosine phosphorylase (MTAP), that is elevated in MTAP-deleted cancers. This MTA-cooperativity is utilised to exploit the synthetic lethal relationship between PRMT5 and MTAP deletion. The outcome is significantly increased killing efficay against MTAP-null cells compared to cells expressing wild type MTAP. The physicochemical properties of TNG908 support CNS penetration.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 125.45
Molecular weight 409.51
XLogP 0.63
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
Click here for help
Canonical SMILES C[C@H]1CC[C@H](C2=CC3=C(C=C2)SC=N3)N(C1)C(=O)C(=O)NC4=CC(=C(N)N=C4)C
Isomeric SMILES NC1=C(C=C(C=N1)NC(C(=O)N2[C@H](CC[C@@H](C2)C)C=3C=CC4=C(N=CS4)C3)=O)C
InChI InChI=1S/C21H23N5O2S/c1-12-3-5-17(14-4-6-18-16(8-14)24-11-29-18)26(10-12)21(28)20(27)25-15-7-13(2)19(22)23-9-15/h4,6-9,11-12,17H,3,5,10H2,1-2H3,(H2,22,23)(H,25,27)/t12-,17+/m0/s1
InChI Key NXXBDYHMHHINFC-YVEFUNNKSA-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/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-(6-amino-5-methylpyridin-3-yl)-2-[(2R,5S)-2-(1,3-benzothiazol-5-yl)-5-methylpiperidin-1-yl]-2-oxoacetamide
Synonyms Click here for help
TNG-908
Database Links Click here for help
CAS Registry No. 2760481-53-4 (source: PubChem)
GtoPdb PubChem SID 496703290
PubChem CID 164753116
RCSB PDB Ligand A1AAV
Search Google for chemical match using the InChIKey NXXBDYHMHHINFC-YVEFUNNKSA-N
Search Google for chemicals with the same backbone NXXBDYHMHHINFC
UniChem Compound Search for chemical match using the InChIKey NXXBDYHMHHINFC-YVEFUNNKSA-N
UniChem Connectivity Search for chemical match using the InChIKey NXXBDYHMHHINFC-YVEFUNNKSA-N