belnacasan   Click here for help

GtoPdb Ligand ID: 9035

Synonyms: HMR3480 | VX-765
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Belnacasan is a prodrug of VRT-043198, a caspase-1 inhibitor that was developed by Vertex. Pharmacological inhibition of caspase-1 is being investigated as a mechanism to reduce pro-inflammatory cytokine (predominantly IL-1β) production as a novel treatment of inflammatory diseases [1]. Inhibition of caspase-1 is a small molecule strategy developed as an alternative to the use of anti-IL-1β neutralising antibodies, such as canakinumab, or the dimeric fusion protein rilonacept that acts as a IL-1 trap.
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 10
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 140.06
Molecular weight 508.21
XLogP 2
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 CCOC1OC(=O)CC1NC(=O)C1CCCN1C(=O)C(C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N
Isomeric SMILES CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N
InChI InChI=1S/C24H33ClN4O6/c1-5-34-23-16(12-18(30)35-23)27-21(32)17-7-6-10-29(17)22(33)19(24(2,3)4)28-20(31)13-8-9-15(26)14(25)11-13/h8-9,11,16-17,19,23H,5-7,10,12,26H2,1-4H3,(H,27,32)(H,28,31)/t16-,17-,19+,23+/m0/s1
InChI Key SJDDOCKBXFJEJB-MOKWFATOSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form VRT-043198
IUPAC Name Click here for help
(2S)-1-[(2S)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
Synonyms Click here for help
HMR3480 | VX-765
Database Links Click here for help
GtoPdb PubChem SID 315661120
PubChem CID 11398092
Search Google for chemical match using the InChIKey SJDDOCKBXFJEJB-MOKWFATOSA-N
Search Google for chemicals with the same backbone SJDDOCKBXFJEJB
UniChem Compound Search for chemical match using the InChIKey SJDDOCKBXFJEJB-MOKWFATOSA-N
UniChem Connectivity Search for chemical match using the InChIKey SJDDOCKBXFJEJB-MOKWFATOSA-N