desidustat   Click here for help

GtoPdb Ligand ID: 12285

Synonyms: EXAMPLE 2 [WO2014102818A1] | Oxemia® | ZYAN-1 | ZYAN1
Compound class: Synthetic organic
Comment: Desidustat (ZYAN1) is an orally bioavailable inhibitor of hypoxia-inducible factor prolyl hydroxylase (HIF-PH) enzymes (PHD1, PHD2, and PHD3; genes EGLN2, EGLN1 and EGLN3 respectively) [5]. It was developed as a strategy to promote erythropoietin (EPO) synthesis and erythropoiesis by stabilising HIF-α transcription factors, as a mechanism to treat anemia associated with chronic diseases. Orally active HIF-PH inhibitors are being exploited as alternatives to injectable erythropoietin stimulating drugs, such as epoetin and darbepoetin, to treat anemia.
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 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 117.86
Molecular weight 332.1
XLogP 2.61
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)CNC(=O)c1c(O)c2ccccc2n(c1=O)OCC1CC1
Isomeric SMILES C1CC1COn1c2ccccc2c(c(c1=O)C(=O)NCC(=O)O)O
InChI InChI=1S/C16H16N2O6/c19-12(20)7-17-15(22)13-14(21)10-3-1-2-4-11(10)18(16(13)23)24-8-9-5-6-9/h1-4,9,21H,5-8H2,(H,17,22)(H,19,20)
InChI Key IKRKQQLJYBAPQT-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
2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]acetic acid
International Nonproprietary Names Click here for help
INN number INN
10542 desidustat
Synonyms Click here for help
EXAMPLE 2 [WO2014102818A1] | Oxemia® | ZYAN-1 | ZYAN1
Database Links Click here for help
CAS Registry No. 1616690-16-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL4650314
GtoPdb PubChem SID 473153873
PubChem CID 75593290
Search Google for chemical match using the InChIKey IKRKQQLJYBAPQT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IKRKQQLJYBAPQT
Search PubMed clinical trials desidustat
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Search PubMed titles/abstracts desidustat
UniChem Compound Search for chemical match using the InChIKey IKRKQQLJYBAPQT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IKRKQQLJYBAPQT-UHFFFAOYSA-N