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TEC4   Click here for help

GtoPdb Ligand ID: 13872

Compound class: Synthetic organic
Comment: TEC4 is an experimental example of a novel protein degrader, called a ByeTAC [1]. Like PROTACs, TEC4 is a bifunctional molecule that carries a warhead to engage the protein of interest (POI), and a second moiety that rather than recruiting to the E3 ubiquitin ligase cascade as per PROTACs, engages with the RPN13 ubiquitin receptor within the 19S RP region of the 26S proteasome to mediate direct proteasomal degradation in a ubiquitin-independent manner. In this case the POI is BRD4 and is bound using the ligand (+)-JQ1. The small molecule TCL-1 is utilised to bind RPN13 [2].
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 16
Hydrogen bond donors 2
Rotatable bonds 25
Topological polar surface area 226.36
Molecular weight 1078.93
XLogP 4.37
No. Lipinski's rules broken 3

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 CC1=C(C)SC2=C1C(=N[C@@H](CC(=O)NCCOCCOCCOCCOCCNC(=O)CC3C(=NN4C(=NN=C4S3)CC5=CC=C(C=C5)Br)C6=CC=C(C=C6)Cl)C7=NN=C(C)N72)C8=CC=C(C=C8)Cl
Isomeric SMILES BrC=1C=CC(=CC1)CC2=NN=C3SC(CC(NCCOCCOCCOCCOCCNC(C[C@H]4C5=NN=C(C)N5C6=C(C(C)=C(C)S6)C(C7=CC=C(Cl)C=C7)=N4)=O)=O)C(=NN32)C8=CC=C(Cl)C=C8
InChI InChI=1S/C48H51BrCl2N10O6S2/c1-29-30(2)68-47-43(29)45(34-8-14-37(51)15-9-34)54-38(46-57-55-31(3)60(46)47)27-41(62)52-16-18-64-20-22-66-24-25-67-23-21-65-19-17-53-42(63)28-39-44(33-6-12-36(50)13-7-33)59-61-40(56-58-48(61)69-39)26-32-4-10-35(49)11-5-32/h4-15,38-39H,16-28H2,1-3H3,(H,52,62)(H,53,63)/t38-,39?/m0/s1
InChI Key PGBWEUBGHMYSIG-SQTCDLSVSA-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel