TTI-101   Click here for help

GtoPdb Ligand ID: 12268

Synonyms: C188-9 [2] | TTI 101 | TTI101
Compound class: Synthetic organic
Comment: TTI-101(formerly C188-9) is an orally bioavailable STAT3 transcription factor inhibitor. It blocks the tyrosine residue phosphorylation by Janus kinase (JAK) that mediates STAT3 activation, leading to downregulation of STAT3-mediated gene expression. This mechanism of action is considered as a valid approach for the treatment of inflammation, fibrosis, and a range of cancers [1,3].

TTI-101 is commercially available from our sponsors

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 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 104.24
Molecular weight 471.11
XLogP 6.29
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 COc1ccc(cc1)S(=O)(=O)Nc1cc(c(c2c1cccc2)O)c1c(O)ccc2c1cccc2
Isomeric SMILES COc1ccc(cc1)S(=O)(=O)Nc1cc(c(c2ccccc12)O)c1c(ccc2ccccc12)O
InChI InChI=1S/C27H21NO5S/c1-33-18-11-13-19(14-12-18)34(31,32)28-24-16-23(27(30)22-9-5-4-8-21(22)24)26-20-7-3-2-6-17(20)10-15-25(26)29/h2-16,28-30H,1H3
InChI Key QDCJDYWGYVPBDO-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[4-hydroxy-3-(2-hydroxynaphthalen-1-yl)naphthalen-1-yl]-4-methoxybenzenesulfonamide
Synonyms Click here for help
C188-9 [2] | TTI 101 | TTI101
Database Links Click here for help
ChEMBL Ligand CHEMBL3392776
GtoPdb PubChem SID 473153856
PubChem CID 1324494
Search Google for chemical match using the InChIKey QDCJDYWGYVPBDO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QDCJDYWGYVPBDO
UniChem Compound Search for chemical match using the InChIKey QDCJDYWGYVPBDO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QDCJDYWGYVPBDO-UHFFFAOYSA-N

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MedChemExpress
C188-9 (links to external site)
Cat. No. HY-112288