5-amino-6-(D-ribitylamino)uracil
Modify Date: 2025-08-25 12:37:24
5-amino-6-(D-ribitylamino)uracil structure
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Common Name | 5-amino-6-(D-ribitylamino)uracil | ||
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| CAS Number | 17014-74-3 | Molecular Weight | 276.24700 | |
| Density | 1.7±0.1 g/cm3 | Boiling Point | N/A | |
| Molecular Formula | C9H16N4O6 | Melting Point | N/A | |
| MSDS | N/A | Flash Point | N/A | |
Use of 5-amino-6-(D-ribitylamino)uracil5-Amino-6-(D-ribitylamino)uracil (5-A-RU) is a precursor of bacterial Riboflavin. 5-Amino-6-(D-ribitylamino)uracil is a mucosal-associated invariant T (MAIT) cells activator. 5-Amino-6-(D-ribitylamino)uracil forms potent MAIT-activating antigens via non-enzymatic reactions with small molecules, such as glyoxal and methylglyoxal, which are derived from other metabolic pathways[1][2][3]. |
| Name | 5-amino-6-(D-ribitylamino)uracil |
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| Synonym | More Synonyms |
| Description | 5-Amino-6-(D-ribitylamino)uracil (5-A-RU) is a precursor of bacterial Riboflavin. 5-Amino-6-(D-ribitylamino)uracil is a mucosal-associated invariant T (MAIT) cells activator. 5-Amino-6-(D-ribitylamino)uracil forms potent MAIT-activating antigens via non-enzymatic reactions with small molecules, such as glyoxal and methylglyoxal, which are derived from other metabolic pathways[1][2][3]. |
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| Related Catalog | |
| In Vitro | The MAIT antigens formed by the reactions between 5-Amino-6-(D-ribitylamino)uracil and glyoxal/methylglyoxal are simple adducts, 5-(2-oxoethylideneamino)-6-D-ribitylaminouracil (5-OE-RU) and 5-(2-oxopropylideneamino)-6-D-ribitylaminouracil (5-OP-RU), respectively, which bound to MR1 as shown by crystal structures of MAIT TCR ternary complexes[1]. 5-A-RU presents in diverse bacteria and yeast as well as plants. 5-A-RU plays an important role in MAIT cell activation, MR1 could not be refolded efficiently with 5-ARU alone. 5-A-RU is a precursor for MAIT cell ligand[2]. 5-A-RU can react extemporaneously with glyoxal and methylglyoxal to generate pyrimidine adducts that activate mouse MAIT cells from STg (iVa19) and DTg (iVa19Vb6) animals[3]. |
| In Vivo | 5-A-RU (100 nM; i.p.; 18 hours) and methylglyoxal (MeG) are mixed extemporaneously, MAIT cells are activated in iVa19 Cα-/- Tg mice (generated on the C57BL/6 background)[3]. |
| References |
| Density | 1.7±0.1 g/cm3 |
|---|---|
| Molecular Formula | C9H16N4O6 |
| Molecular Weight | 276.24700 |
| Exact Mass | 276.10700 |
| PSA | 184.69000 |
| LogP | -3.84 |
| Index of Refraction | 1.676 |
| InChIKey | XKQZIXVJVUPORE-RPDRRWSUSA-N |
| SMILES | Nc1c(NCC(O)C(O)C(O)CO)[nH]c(=O)[nH]c1=O |
| 1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)amino]-1-deoxy-D-ribitol |
| D-Ribitol, 1-[(5-amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinyl)amino]-1-deoxy- |