Ketcher 05142009402D 1   1.00000     0.00000     0

 22 22  0     1  0            999 V2000
   10.7672  -89.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284  -90.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6351  -91.3695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5026  -91.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5026  -92.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3631  -91.3800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3698  -93.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6354  -93.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2303  -91.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2370  -92.8704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3698  -94.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0976  -91.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6363  -94.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690  -94.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7698  -95.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9010  -94.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284  -88.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7609  -88.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4961  -88.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3637  -88.3756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9012  -90.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8918  -88.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0     0  0
  3  4  1  0     0  0
  4  5  2  0     0  0
  4  6  1  0     0  0
  5  7  1  0     0  0
  5  8  1  0     0  0
  6  9  1  0     0  0
  7 10  1  0     0  0
  7 11  2  0     0  0
  9 12  2  0     0  0
  9 10  1  0     0  0
  8 13  2  0     0  0
 13 14  1  0     0  0
 14 15  2  0     0  0
 14 16  1  0     0  0
 17 18  1  0     0  0
  2  1  1  0     0  0
 18  1  1  0     0  0
 17 19  1  0     0  0
 19 20  1  0     0  0
  1 21  1  6     0  0
 18 22  1  6     0  0
M  END
> <ID>
CHEBI:149744

> <NAME>
6-[(1,4-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil

> <DEFINITION>
A nucleobase analogue that is uracil substituted with a (1,4-dideoxy-D-ribityl)amino group at position 6 and an (E)-(2-oxopropylidene)amino 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).

> <STAR>
3

> <SYNONYM>
6-[(1,4-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil; 4'-D-5-OP-RU; 1,4-dideoxy-1-[[1,2,3,6-tetrahydro-2,6-dioxo-5-[[(1E)-2-oxopropylidene]amino]-4-pyrimidinyl]amino]-D-erythro-pentitol

> <IUPAC_NAME>
1,4-dideoxy-1-({2,6-dioxo-5-[(E)-(2-oxopropylidene)amino]-1,2,3,6-tetrahydropyrimidin-4-yl}amino)-D-erythro-pentitol

> <FORMULA>
C12H18N4O6

> <MASS>
314.298

> <MONOISOTOPIC_MASS>
314.12263

> <CHARGE>
0

> <SMILES>
[C@H](CNC1=C(C(NC(N1)=O)=O)/N=C/C(=O)C)([C@@H](CCO)O)O

> <INCHI>
InChI=1S/C12H18N4O6/c1-6(18)4-13-9-10(15-12(22)16-11(9)21)14-5-8(20)7(19)2-3-17/h4,7-8,17,19-20H,2-3,5H2,1H3,(H3,14,15,16,21,22)/b13-4+/t7-,8+/m1/s1

> <INCHIKEY>
LFFDRPXUQKVYPE-ZGBHKRMMSA-N

> <PUBMED_CITATION>
32123373

$$$$