venglustat   Click here for help

GtoPdb Ligand ID: 11550

Synonyms: Genz-682452 | GZ/SAR402671 | ibiglustat | SAR402671
PDB Ligand
Compound class: Synthetic organic
Comment: Venglustat is a clinical stage oral glucosylceramide synthase (GCS) inhibitor. GCS is encoded by the UGCG gene. It was developed for potential to treat diseases in which the glycolipid glucosylceramide accumulates and leads to lysosomal dysfunction and organ damage [3-4]. Venglustat inhibits glucosylceramide synthesis. Its chemical structure is claimed in Genzyme's patent WO2012129084A2 [1]. It has subsequently been reported to act as a substrate-competitive inhibitor of N-terminal Xaa-Pro-Lys N-methyltransferase 1 (NTMT1; Q9BV86; IC50 420 nM) [2].

The venglustat analogue GENZ-667161 and the eliglustat analogue GENZ-123346 have been shown to inhibit replication of SARS-CoV-2 in vitro [5], potentially by disrupting the host cell membrane dynamics which the virions depend upon for infection.
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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 CDK toolkit. 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 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 82.7
Molecular weight 389.16
XLogP 3.27
No. Lipinski's rules broken 0
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.

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Canonical SMILES O=C(NC(c1csc(n1)c1ccc(cc1)F)(C)C)O[C@@H]1CN2CCC1CC2
Isomeric SMILES O=C(NC(c1csc(n1)c1ccc(cc1)F)(C)C)O[C@@H]1CN2CCC1CC2
InChI InChI=1S/C20H24FN3O2S/c1-20(2,17-12-27-18(22-17)14-3-5-15(21)6-4-14)23-19(25)26-16-11-24-9-7-13(16)8-10-24/h3-6,12-13,16H,7-11H2,1-2H3,(H,23,25)/t16-/m1/s1
InChI Key YFHRCLAKZBDRHN-MRXNPFEDSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(3S)-1-azabicyclo[2.2.2]octan-3-yl] N-[2-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]propan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
10063 venglustat
Synonyms Click here for help
Genz-682452 | GZ/SAR402671 | ibiglustat | SAR402671
Database Links Click here for help
CAS Registry No. 1401090-53-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297611
DrugBank Ligand DB14966
GtoPdb PubChem SID 441604922
PubChem CID 60199242
RCSB PDB Ligand KYF
Search Google for chemical match using the InChIKey YFHRCLAKZBDRHN-MRXNPFEDSA-N
Search Google for chemicals with the same backbone YFHRCLAKZBDRHN
Search PubMed clinical trials venglustat
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UniChem Compound Search for chemical match using the InChIKey YFHRCLAKZBDRHN-MRXNPFEDSA-N
UniChem Connectivity Search for chemical match using the InChIKey YFHRCLAKZBDRHN-MRXNPFEDSA-N