CHEBI:149750 - 8-(4-hydroxybutyl)-7-methyllumazine

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ChEBI Name 8-(4-hydroxybutyl)-7-methyllumazine ChEBI ID CHEBI:149750 Definition A pteridine that is lumazine substituted with a 4-hydroxybutyl group at position 8 and a methyl group at position 7; one of 20 modifications to the potent microbial riboflavin-based metabolite antigen 5-(2-oxopropylideneamino)-6-D-ribityl aminouracil (5-OP-RU), an activator of mucosal-associated invariant T (MAIT) cells when presented by the MR1 protein (reported in MED:32123373). Stars This entity has been manually annotated by the ChEBI Team. Supplier Information No supplier information found for this compound. Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C11H14N4O3 Net Charge 0 Average Mass 250.258 Monoisotopic Mass 250.10659 InChI InChI=1S/C11H14N4O3/c1-7-6-12-8-9(13-11(18)14-10(8)17)15(7)4-2-3-5-16/h6,16H,2-5H2,1H3,(H,14,17,18) InChIKey DQLAXLXJOAVJPS-UHFFFAOYSA-N SMILES N1C(N=C2C(C1=O)=NC=C(N2CCCCO)C)=O ChEBI Ontology Outgoing 8-(4-hydroxybutyl)-7-methyllumazine (CHEBI:149750) has functional parent lumazine (CHEBI:16489) 8-(4-hydroxybutyl)-7-methyllumazine (CHEBI:149750) is a pteridines (CHEBI:26373) IUPAC Name 8-(4-hydroxybutyl)-7-methylpteridine-2,4(3H,8H)-dione Synonyms Sources 4'-OH-butyl-L-7-Me ChEBI 8-(4-hydroxybutyl)-7-methyl-2,4(3H,8H)-pteridinedione ChEBI Citation Awad W, Ler GJM, Xu W, Keller AN, Mak JYW, Lim XY, Liu L, Eckle SBG, Le Nours J, McCluskey J, Corbett AJ, Fairlie DP, Rossjohn J (2020) The molecular basis underpinning the potency and specificity of MAIT cell antigens. Nature immunology 21, 400-411 [PubMed:32123373] [show Abstract] Mucosal-associated invariant T (MAIT) cells are activated by microbial riboflavin-based metabolite antigens when presented by MR1. How modifications to the potent antigen 5-OP-RU affect presentation by MR1 and MAIT cell activation remains unclear. Here we design 20 derivatives, termed altered metabolite ligands (AMLs), to dissect the impact of different antigen components on the human MAIT-MR1 axis. Analysis of 11 crystal structures of MAIT T cell antigen receptor (TCR)-MR1-AML ternary complexes, along with biochemical and functional assays, shows that MR1 cell-surface upregulation is influenced by ribityl and non-ribityl components of the ligand and the hydrophobicity of the MR1-AML interface. The polar ribityl chain of the AML strongly influences MAIT cell activation potency through dynamic compensatory interactions within a MAIT TCR-MR1-AML interaction triad. We define the basis by which the MAIT TCR can differentially recognize AMLs, thereby providing insight into MAIT cell antigen specificity and potency. Last Modified 14 May 2020