TTK21   Click here for help

GtoPdb Ligand ID: 12197

Synonyms: TTK-21
Compound class: Synthetic organic
Comment: TTK21 is a small molecule activator of CREB-binding protein (CREBBP) and p300 (EP300) histone acetyltransferases [2]. It reaches the brain when administered intraperitonealy as a glucose-based carbon nanosphere conjugate. TTK21 induces axon regeneration in in vivo models of spinal injury [3] and neurodegeneration [1-2,4].
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 2
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 38.33
Molecular weight 357.07
XLogP 5.24
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 CCCOc1ccccc1C(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
Isomeric SMILES CCCOc1ccccc1C(=O)Nc1cc(c(cc1)Cl)C(F)(F)F
InChI InChI=1S/C17H15ClF3NO2/c1-2-9-24-15-6-4-3-5-12(15)16(23)22-11-7-8-14(18)13(10-11)17(19,20)21/h3-8,10H,2,9H2,1H3,(H,22,23)
InChI Key AQJBXYBDNZHZRE-UHFFFAOYSA-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. Chatterjee S, Cassel R, Schneider-Anthony A, Merienne K, Cosquer B, Tzeplaeff L, Halder Sinha S, Kumar M, Chaturbedy P, Eswaramoorthy M et al.. (2018)
Reinstating plasticity and memory in a tauopathy mouse model with an acetyltransferase activator.
EMBO Mol Med, 10 (11): e8587. [PMID:30275019]
2. Chatterjee S, Mizar P, Cassel R, Neidl R, Selvi BR, Mohankrishna DV, Vedamurthy BM, Schneider A, Bousiges O, Mathis C et al.. (2013)
A novel activator of CBP/p300 acetyltransferases promotes neurogenesis and extends memory duration in adult mice.
J Neurosci, 33 (26): 10698-712. [PMID:23804093]
3. Müller F, De Virgiliis F, Kong G, Zhou L, Serger E, Chadwick J, Sanchez-Vassopoulos A, Singh AK, Eswaramoorthy M, Kundu TK et al.. (2022)
CBP/p300 activation promotes axon growth, sprouting, and synaptic plasticity in chronic experimental spinal cord injury with severe disability.
PLoS Biol, 20 (9): e3001310. [PMID:36126035]
4. Singh AK, Neo SH, Liwang C, Pang KKL, Leng JCK, Sinha SH, Shetty MS, Vasudevan M, Rao VJ, Joshi I et al.. (2022)
Glucose derived carbon nanosphere (CSP) conjugated TTK21, an activator of the histone acetyltransferases CBP/p300, ameliorates amyloid-beta 1-42 induced deficits in plasticity and associativity in hippocampal CA1 pyramidal neurons.
Aging Cell, 21 (9): e13675. [PMID:35962576]