CHEBI:149716 - 6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil

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ChEBI Name 6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil
ChEBI ID CHEBI:149716
ChEBI ASCII Name 6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil
Definition A nucleobase analogue that is uracil substituted with a (1-deoxy-D-ribityl)methyl group at position 6 and a (1E)-3-oxobut-1-en-1-yl group at position 5; 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
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Formula C14H20N2O7
Net Charge 0
Average Mass 328.321
Monoisotopic Mass 328.12705
InChI InChI=1S/C14H20N2O7/c1-7(18)2-3-8-9(15-14(23)16-13(8)22)4-5-10(19)12(21)11(20)6-17/h2-3,10-12,17,19-21H,4-6H2,1H3,(H2,15,16,22,23)/b3-2+/t10-,11+,12-/m0/s1
InChIKey YIGUGMFHMVTCHU-VUGGRDAHSA-N
SMILES [C@H](O)(CCC1=C(C(NC(N1)=O)=O)/C=C/C(=O)C)[C@@H]([C@@H](CO)O)O
Roles Classification
Biological Role(s): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
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ChEBI Ontology
Outgoing 6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149716) has functional parent uracil (CHEBI:17568)
6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149716) has role epitope (CHEBI:53000)
6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149716) is a nucleobase analogue (CHEBI:67142)
6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149716) is a pyrimidone (CHEBI:38337)
IUPAC Name
1,2-dideoxy-1-{2,6-dioxo-5-[(1E)-3-oxobut-1-en-1-yl]-1,2,3,6-tetrahydropyrimidin-4-yl}-D-ribo-hexitol
Synonym Source
1,2-dideoxy-1-[1,2,3,6-tetrahydro-2,6-dioxo-5-[(1E)-3-oxo-1-buten-1-yl]-4-pyrimidinyl]-D-ribo-hexitol ChEBI
Citation Waiting for Citations Type Source
32123373 PubMed citation Europe PMC
Last Modified
14 May 2020