tolmetin   Click here for help

GtoPdb Ligand ID: 7311

Synonyms: MCN-2559 | McN-2559-21-98 | Tolectin®
Approved drug PDB Ligand Immunopharmacology Ligand
tolmetin is an approved drug (FDA (1976))
Compound class: Synthetic organic
Comment: Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic activity.
Marketed formulations may contain tolmetin sodium (PubChem CID 23665411).
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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 59.3
Molecular weight 257.11
XLogP 2.56
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 OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
Isomeric SMILES OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
InChI InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChI Key UPSPUYADGBWSHF-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
Ligand families/groups Non-steroidal anti-inflammatory ligands
Approved drug? Yes (FDA (1976))
IUPAC Name Click here for help
2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
2861 tolmetin
Synonyms Click here for help
MCN-2559 | McN-2559-21-98 | Tolectin®
Database Links Click here for help
CAS Registry No. 26171-23-3
ChEMBL Ligand CHEMBL1020
DrugBank Ligand DB00500
DrugCentral Ligand 2699
GtoPdb PubChem SID 178103884
PubChem CID 5509
RCSB PDB Ligand TLT
Search Google for chemical match using the InChIKey UPSPUYADGBWSHF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UPSPUYADGBWSHF
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UniChem Compound Search for chemical match using the InChIKey UPSPUYADGBWSHF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UPSPUYADGBWSHF-UHFFFAOYSA-N
Wikipedia Tolmetin