LM10   Click here for help

GtoPdb Ligand ID: 9016

Synonyms: LM-10
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: LM10 is an experimental compound reported as an inhibitor of tryptophan 2,3-dioxygenase (TDO2), with anti-neoplastic activity in a murine syngeneic tumour model [1-2].
The closest structural match on PubChem (CID 91885138) is an alternative representation, with different double bond specification across the vinyl group linking the indole and tetrazole groups.
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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 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 70.25
Molecular weight 229.08
XLogP 2.86
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 Fc1ccc2c(c1)[nH]cc2C=Cc1nnn[nH]1
Isomeric SMILES Fc1ccc2c(c1)[nH]cc2/C=C/c1nnn[nH]1
InChI InChI=1S/C11H8FN5/c12-8-2-3-9-7(6-13-10(9)5-8)1-4-11-14-16-17-15-11/h1-6,13H,(H,14,15,16,17)/b4-1+
InChI Key JDBSZVDIUIRSDG-DAFODLJHSA-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/)
Bioactivity Comments
Tryptophan catabolism is an important mechanism contributing to tumoural immune resistance. Like IDO, a drug target being actively pursued, TDO2 also catabolises tryptophan. Inhibition of tryptophan degradation is able to reverse the immune tolerance which permits tumour cells to evade immune system detection and destruction.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
tryptophan 2,3-dioxygenase Primary target of this compound Hs Inhibitor Inhibition 5.3 pKi - 1-2
⤷ pKi 5.3 (Ki 5.6x10-6 M) [1-2]
tryptophan 2,3-dioxygenase Primary target of this compound Hs Inhibitor Inhibition 6.2 pIC50 - 2
⤷ pIC50 6.2 (IC50 6.2x10-7 M) [2]
Description: Concentration inhibiting TDO activity by 50% in a cellular assay, at 80μM L-tryptophan.
tryptophan 2,3-dioxygenase Mm Inhibitor Inhibition 5.7 pIC50 - 2
⤷ pIC50 5.7 (IC50 1.96x10-6 M) [2]
Description: Concentration inhibiting TDO activity by 50% in a cellular assay, at 80μM L-tryptophan.