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VT3989   Click here for help

GtoPdb Ligand ID: 13867

Synonyms: compound 24 [WO2020214734A1] | VT-3989
Compound class: Synthetic organic
Comment: VT3989 is an orally bioavailable YAP/TAZ inhibitor that is proposed for antineoplastic potential. The structure is claimed in Vivace Therapeutics' patent WO2020214734A1 [2]. VT3989 inhibits YAP function and subsequent TEAD palmitoylation that would otherwise drive activation of transcriptional enhancer associate domain (TEAD) transcription factors that promote cell proliferation [3]. Hyperactivation of the Hippo-YAP/TAZ-TEAD pathway is implicated in tumour progression [1].
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 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 58.56
Molecular weight 389.37
XLogP 2.2
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 C[C@H](CO)NC(=O)C1=CC=C2C(=C1)C=CC=C2OC3=CC=C(C=C3)C(F)(F)F
Isomeric SMILES C[C@H](CO)NC(=O)C1=CC2=CC=CC(OC3=CC=C(C=C3)C(F)(F)F)=C2C=C1
InChI InChI=1S/C21H18F3NO3/c1-13(12-26)25-20(27)15-5-10-18-14(11-15)3-2-4-19(18)28-17-8-6-16(7-9-17)21(22,23)24/h2-11,13,26H,12H2,1H3,(H,25,27)/t13-/m1/s1
InChI Key FJIVCOAHSKDOAC-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/)
References
1. Harvey KF, Zhang X, Thomas DM. (2013)
The Hippo pathway and human cancer.
Nat Rev Cancer, 13 (4): 246-57. [PMID:23467301]
2. Konradi AW, Lin TTLT. (2020)
Bicyclic compounds.
Patent number: WO2020214734A1. Assignee: Vivace Therapeutics, Inc.. Priority date: 15/04/2020. Publication date: 22/10/2020.
3. Ma S, Meng Z, Chen R, Guan KL. (2019)
The Hippo Pathway: Biology and Pathophysiology.
Annu Rev Biochem, 88: 577-604. [PMID:30566373]