navoximod   

GtoPdb Ligand ID: 9019

Synonyms: GDC-0919 | NLG-919 | NLG919 | RG6078
Compound class: Synthetic organic
Comment: Navoximod (NLG-919) is a potent inhibitor of indoleamine-2,3-dioxygenase (IDO1) that was developed by Genentech and NewLink Genetics [2-3]. IOD1 is the first and rate-limiting component of the pathway mediating metabolism of tryptophan to kynurenine. Tryptophan depletion enhances the number and function of the Treg (suppressive) arm of the immune system and inhibits the effector T cell (stimulatory) arm. This action of IDO1 facilitates acquired local and peripheral immune tolerance in normal and pathological conditions. IOD1 inhibitors are being developed as novel therapeutics to reverse the immunosuppression associated with cancer.
The crystal structure of human IDO1 in complex with navoximod has been submitted to the PDB with ID 6O3I [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 38.05
Molecular weight 282.17
XLogP 4.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(C1CCCCC1)CC1c2ccccc2c2n1cnc2
Isomeric SMILES OC(C1CCCCC1)CC1c2ccccc2c2n1cnc2
InChI InChI=1S/C18H22N2O/c21-18(13-6-2-1-3-7-13)10-16-14-8-4-5-9-15(14)17-11-19-12-20(16)17/h4-5,8-9,11-13,16,18,21H,1-3,6-7,10H2
InChI Key YTRRAUACYORZLX-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanol
International Nonproprietary Names
INN number INN
10392 navoximod
Synonyms
GDC-0919 | NLG-919 | NLG919 | RG6078
Database Links
CAS Registry No. 1402836-58-1 (source: PubChem)
ChEMBL Ligand CHEMBL3629569
GtoPdb PubChem SID 315661104
PubChem CID 66558287
RCSB PDB Ligand LKP
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SynPHARM 83385 (in complex with indoleamine 2,3-dioxygenase 1)