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GtoPdb Ligand ID: 9621

Synonyms: Example 230 [US7858621] | PAC-14028
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Asivatrep (PAC-14028) is an antagonist of the transient receptor potential vanilloid type 1 (TRPV1) channel, developed by AmorePacific for anti-inflammatory potential in refractory dermatoses [2]. It is claimed as example 230 in patent US7858621 [1]. PAC-14028 is administered topically for skin inflammation.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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 6
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 96.54
Molecular weight 491.13
XLogP 4.4
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 CCCc1nc(ccc1C=CC(=O)NC(c1cc(F)c(c(c1)F)NS(=O)(=O)C)C)C(F)(F)F
Isomeric SMILES CCCc1nc(ccc1/C=C/C(=O)N[C@@H](c1cc(F)c(c(c1)F)NS(=O)(=O)C)C)C(F)(F)F
InChI InChI=1S/C21H22F5N3O3S/c1-4-5-17-13(6-8-18(28-17)21(24,25)26)7-9-19(30)27-12(2)14-10-15(22)20(16(23)11-14)29-33(3,31)32/h6-12,29H,4-5H2,1-3H3,(H,27,30)/b9-7+/t12-/m1/s1
InChI Key UKGJZDSUJSPAJL-YPUOHESYSA-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/)
Immunopharmacology Comments
Activation of TRPV1 can initiate the sensation of burning pain and prime the release of pro-inflammatory neuropeptides like substance P (SP) and calcitonin gene-related peptide (CGRP), that can induce or augment neurogenic inflammation. Studies in Trpv1 knockout mice indicate a role for this channel in the integration of pain and neurogenic inflammation. TRPV1 antagonism is considered to be a novel pharmacotherapeutic approach to mitigate the unmet medical needs of modulating nociceptive responses and neurogenic inflammation, without serious adverse effects.
Immunopharmacology Disease
Disease X-Refs Comment References
Atopic dermatitis Disease Ontology: DOID:3310
OMIM: 603165
 Phase 3 clinical candidate for atopic dermatitis.