GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

DF2726   Click here for help

GtoPdb Ligand ID: 12231

Synonyms: DF2726 (acid form) | DF2726A (sodium salt)
Compound class: Synthetic organic
Comment: DF2726 is a non-competitive, negative allosteric modulator of CXCL8 (IL-8) signalling via its endogenous chemokine receptors CXCR1 and CXCR2 [1]. Its chemical structure was claimed in patent EP3192504A1 [2], and it appears to be structurally related to DF2755A. Activation of the IL-8 pathway has been linked to the development of chemotherapy-induced neuropathic pain. It is predicted that inhibition of this mechanism might offer clinical utility for cancer patients who experience chemotherapy-induced peripheral neuropathy [1].
DF2726A refers to the sodium salt formulation that is used for in vitro and in vivo studies.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 90.46
Molecular weight 330.33
XLogP 3.41
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
Click here for help

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/)

✖
Canonical SMILES OC(=O)C(c1ccc(cc1)Nc1scc(n1)C(F)(F)F)(C)C
Isomeric SMILES CC(C(=O)O)(C)c1ccc(cc1)Nc1scc(n1)C(F)(F)F
InChI InChI=1S/C14H13F3N2O2S/c1-13(2,11(20)21)8-3-5-9(6-4-8)18-12-19-10(7-22-12)14(15,16)17/h3-7H,1-2H3,(H,18,19)(H,20,21)
InChI Key TVKXUJXIOMUVFS-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
2-methyl-2-[4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino]phenyl]propanoic acid
Synonyms Click here for help
DF2726 (acid form) | DF2726A (sodium salt)
Database Links Click here for help
GtoPdb PubChem SID 473153819
PubChem CID 45110930
Search Google for chemical match using the InChIKey TVKXUJXIOMUVFS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone TVKXUJXIOMUVFS
UniChem Compound Search for chemical match using the InChIKey TVKXUJXIOMUVFS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TVKXUJXIOMUVFS-UHFFFAOYSA-N