tryptanthrin 5i   Click here for help

GtoPdb Ligand ID: 10126

Synonyms: compound 5i [PMID: 24099220]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 5i is a tryptanthrin analogue that acts as an inhibitor of indoleamine 2, 3-dioxygenase (IDO) 1 and IDO2 [1-2]. It is a non-competitive inhibitor of IDO2.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 94.58
Molecular weight 293.04
XLogP 2.68
No. Lipinski's rules broken 0
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Canonical SMILES [O-][N+](=O)c1ccc2c(c1)C(=O)c1n2c(=O)c2c(n1)cccc2
Isomeric SMILES [O-][N+](=O)c1ccc2c(c1)C(=O)c1n2c(=O)c2c(n1)cccc2
InChI InChI=1S/C15H7N3O4/c19-13-10-7-8(18(21)22)5-6-12(10)17-14(13)16-11-4-2-1-3-9(11)15(17)20/h1-7H
Immunopharmacology Comments
Inhibiting IDO1 helps restore immune surveillance and immune cell-directed killing of tumour cells [2], making IDO1 a tractable immunotherapy drug target. However, despite promising preclinical findingds and positive clinical results vis a vis safety of compounds such as epacadostat, therapeutic efficacy has not yet been established.