DDTPA   Click here for help

GtoPdb Ligand ID: 12967

Synonyms: compound 74 [PMID: 33540044]
Compound class: Synthetic organic
Comment: DDTPA is an orally bioavailable P2X3 ion channel antagonist [1]. It is an analogue of the clinical lead sivopixant (S-600918). DDTPA exhibits higher affinity and high selectivity for hP2X3 homotrimeric ATP-gated ion channels compared to hP2X2/3 heterotrimeric channels in vitro. DDTPA appears to have an allosteric mode of action [2]. This compound was not considered as a clinical candidate due to the predicted high dose required in humans to produce the pharmacodynamic effect. It provides a suitable P2X3 selective tool for in vitro experiments and non-primate animal model studies.
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 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 111.54
Molecular weight 472.92
XLogP 2.61
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 CC(C)OC1=CC=C(C=C1Cl)NC2=NC(=O)N(CCC(=O)O)C(=O)N2CC3=CC=C(C)C=C3
Isomeric SMILES ClC=1C=C(C=CC1OC(C)C)NC=2N(C(N(C(N2)=O)CCC(=O)O)=O)CC3=CC=C(C=C3)C
InChI InChI=1S/C23H25ClN4O5/c1-14(2)33-19-9-8-17(12-18(19)24)25-21-26-22(31)27(11-10-20(29)30)23(32)28(21)13-16-6-4-15(3)5-7-16/h4-9,12,14H,10-11,13H2,1-3H3,(H,29,30)(H,25,26,31)
InChI Key KRHNDEFYSFIWAD-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
3-[4-(3-chloro-4-propan-2-yloxyanilino)-3-[(4-methylphenyl)methyl]-2,6-dioxo-1,3,5-triazin-1-yl]propanoic acid
Synonyms Click here for help
compound 74 [PMID: 33540044]
Database Links Click here for help
GtoPdb PubChem SID 485206088
PubChem CID 68020375
Search Google for chemical match using the InChIKey KRHNDEFYSFIWAD-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KRHNDEFYSFIWAD
UniChem Compound Search for chemical match using the InChIKey KRHNDEFYSFIWAD-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KRHNDEFYSFIWAD-UHFFFAOYSA-N