vopimetostat   Click here for help

GtoPdb Ligand ID: 12902

Synonyms: TNG-462 | TNG462
PDB Ligand
Compound class: Synthetic organic
Comment: TNG-462 (Tango Therapuetics) is a MTA-cooperative protein arginine methyltransferases 5 (PRMT5) inhibitor, that is proposed to treat methylthioadenosine phosphorylase (MTAP) deleted solid tumours. MTAP deficient cancer cells are unable to obtain adenine and methionine from the salvage pathway [1]. Adding inhibition of PRMT5 further decreases the viability of MTAP deficient cancer cells [2]. 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.
The chemical structure of TNG-462 is identical to that for the INN vopimetostat (proposed list 132, Feb. 2025).

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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 8
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 128.69
Molecular weight 520.69
XLogP 1
No. Lipinski's rules broken 1

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 CCC1=C(N)N=CC(=C1)NC(=O)C(=O)N2C[C@@H](C)CC[C@@H]2C3=CC4=C(C=C3)SC(=N4)C5CCN(C)CC5
Isomeric SMILES CCC1=C(N)N=CC(NC(=O)C(=O)N2C[C@@H](C)CC[C@@H]2C3=CC4=C(SC(=N4)C5CCN(C)CC5)C=C3)=C1
InChI InChI=1S/C28H36N6O2S/c1-4-18-13-21(15-30-25(18)29)31-26(35)28(36)34-16-17(2)5-7-23(34)20-6-8-24-22(14-20)32-27(37-24)19-9-11-33(3)12-10-19/h6,8,13-15,17,19,23H,4-5,7,9-12,16H2,1-3H3,(H2,29,30)(H,31,35)/t17-,23+/m0/s1
InChI Key DHAGMIPSRSPWSH-GAJHUEQPSA-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. Bertino JR, Waud WR, Parker WB, Lubin M. (2011)
Targeting tumors that lack methylthioadenosine phosphorylase (MTAP) activity: current strategies.
Cancer Biol Ther, 11 (7): 627-32. [PMID:21301207]
2. Fu S, Zheng Q, Zhang D, Lin C, Ouyang L, Zhang J, Chen L. (2022)
Medicinal chemistry strategies targeting PRMT5 for cancer therapy.
Eur J Med Chem, 244: 114842. [PMID:36274274]