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denifanstat   Click here for help

GtoPdb Ligand ID: 14123

Synonyms: ASC-40 | ASC40 | compound 152 [US8871790] | TVB-2640 | TVB2640
PDB Ligand
Compound class: Synthetic organic
Comment: Denifanstat (TVB-2640, ASC-40) is a fatty acid synthase inhibitor [1,3]. It was designed to reduce excess liver fat and directly inhibit inflammatory and fibrogenic pathways in fatty-liver diseases [2]. Targeting fatty acid synthase has also been investigated for addition to chemotherapeutic regimens [4-7], and for potential to reduce sebum overproduction and inflammation in severe acne.
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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
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 1
Rotatable bonds 5
Topological polar surface area 80.85
Molecular weight 439.55
XLogP 4.07
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 CC1=C(C=C(C(=C1)C2CCC2)C3=NNC(=N3)C)C(=O)N4CCC(CC4)C5=CC=C(C=C5)C#N
Isomeric SMILES CC1=CC(=C(C=C1C(=O)N2CCC(CC2)C3=CC=C(C=C3)C#N)C4=NNC(=N4)C)C5CCC5
InChI InChI=1S/C27H29N5O/c1-17-14-24(22-4-3-5-22)25(26-29-18(2)30-31-26)15-23(17)27(33)32-12-10-21(11-13-32)20-8-6-19(16-28)7-9-20/h6-9,14-15,21-22H,3-5,10-13H2,1-2H3,(H,29,30,31)
InChI Key BBGOSBDSLYHMRA-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
4-[1-[4-cyclobutyl-2-methyl-5-(5-methyl-1H-1,2,4-triazol-3-yl)benzoyl]piperidin-4-yl]benzonitrile
International Nonproprietary Names Click here for help
INN number INN
11784 denifanstat
Synonyms Click here for help
ASC-40 | ASC40 | compound 152 [US8871790] | TVB-2640 | TVB2640
Database Links Click here for help
CAS Registry No. 1399177-37-7 (source: WHO INN record)
ChEBI CHEBI:233413
ChEMBL Ligand CHEMBL3661754
DrugBank Ligand DB17576
PubChem CID 66548316
RCSB PDB Ligand X5O
Search Google for chemical match using the InChIKey BBGOSBDSLYHMRA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BBGOSBDSLYHMRA
Search PubMed clinical trials denifanstat
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UniChem Compound Search for chemical match using the InChIKey BBGOSBDSLYHMRA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BBGOSBDSLYHMRA-UHFFFAOYSA-N