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MetaCyc Compound: 5-amino-6-(D-ribitylamino)uracil

Abbrev Name: ARP

Synonyms: 6-(1-D-ribitylamino)-5-amino-2,4-dihydroxypyrimidine, 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione, ARP, 6-(1-D-ribitylamino)-5-aminouracil, 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione

Citations: [Neidhardt96]

Chemical Formula: C9H16N4O6

Molecular Weight: 276.25 Daltons

Monoisotopic Molecular Weight: 276.106984267 Daltons

SMILES: C(NC1(NC(NC(=O)C(N)=1)=O))C(O)C(O)C(O)CO

InChI: InChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)/t3-,4+,6-/m0/s1

InChIKey: InChIKey=XKQZIXVJVUPORE-RPDRRWSUSA-N

Unification Links: ChEBI:15934 , HMDB:HMDB11106 , IAF1260:44429 , KEGG:C04732 , PubChem:14056325

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -36.68207 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

factor 420 biosynthesis :
5-amino-6-(D-ribitylamino)uracil + 4-hydroxyphenylpyruvate + 2 S-adenosyl-L-methionine + H2O → 7,8-didemethyl-8-hydroxy-5-deazariboflavin + 2 5'-deoxyadenosine + 2 L-methionine + oxalate + ammonium + 3 H+

flavin biosynthesis I (bacteria and plants) , flavin biosynthesis II (archaea) , flavin biosynthesis III (fungi) :
5-amino-6-(D-ribitylamino)uracil + 1-deoxy-L-glycero-tetrulose 4-phosphate → 6,7-dimethyl-8-(1-D-ribityl)lumazine + phosphate + H+ + 2 H2O

Reactions known to produce the compound:

flavin biosynthesis I (bacteria and plants) :
2 6,7-dimethyl-8-(1-D-ribityl)lumazine + H+5-amino-6-(D-ribitylamino)uracil + riboflavin
5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O → 5-amino-6-(D-ribitylamino)uracil + phosphate

flavin biosynthesis II (archaea) :
2 6,7-dimethyl-8-(1-D-ribityl)lumazine + H+5-amino-6-(D-ribitylamino)uracil + riboflavin
5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O → 5-amino-6-(D-ribitylamino)uracil + phosphate

flavin biosynthesis III (fungi) :
2 6,7-dimethyl-8-(1-D-ribityl)lumazine + H+5-amino-6-(D-ribitylamino)uracil + riboflavin
5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O → 5-amino-6-(D-ribitylamino)uracil + phosphate

Credits:
Revised 22-Oct-2013 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Neidhardt96: Neidhardt FC, Curtiss III R, Ingraham JL, Lin ECC, Low Jr KB, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE "Escherichia coli and Salmonella, Cellular and Molecular Biology, Second Edition." American Society for Microbiology, Washington, D.C., 1996.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, biocyc14.