PF-04859989   Click here for help

GtoPdb Ligand ID: 9038

Synonyms: compound 1 [PMID: 23466229]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: PF-04859989 was identified as a potent, irreversable and selective inhibitor of human and rat kynurenine aminotransferase II (KATII; a.k.a. aminoadipate aminotransferase AADAT) [1-2] . An X-ray crystal structure of the enzyme co-crystalised with an inhibitor has been reported [1]. In vivo pharmacokinetic and efficacy studies in rat show it to be brain-penetrant, reducing brain kynurenic acid by 50%. KAT inhibitors are expected to exhibit neuroprotective effects, that may be beneficial for the treatment of neurodegenerative and cognitive impairment disorders [3].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 66.56
Molecular weight 178.07
XLogP 0.43
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
Click here for help

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/)

✖
Canonical SMILES O=C1C(N)Cc2c(N1O)cccc2
Isomeric SMILES O=C1[C@@H](N)Cc2c(N1O)cccc2
InChI InChI=1S/C9H10N2O2/c10-7-5-6-3-1-2-4-8(6)11(13)9(7)12/h1-4,7,13H,5,10H2/t7-/m0/s1
InChI Key HYTRYTZFJVVZAF-ZETCQYMHSA-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
(3S)-3-amino-1-hydroxy-3,4-dihydroquinolin-2-one
Synonyms Click here for help
compound 1 [PMID: 23466229]
Database Links Click here for help
ChEMBL Ligand CHEMBL2047851
GtoPdb PubChem SID 315661123
PubChem CID 22868923
Search Google for chemical match using the InChIKey HYTRYTZFJVVZAF-ZETCQYMHSA-N
Search Google for chemicals with the same backbone HYTRYTZFJVVZAF
UniChem Compound Search for chemical match using the InChIKey HYTRYTZFJVVZAF-ZETCQYMHSA-N
UniChem Connectivity Search for chemical match using the InChIKey HYTRYTZFJVVZAF-ZETCQYMHSA-N