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

Synonyms: 5-amino-6-(5'-phosphoribitylamino)uracil, 5-amino-6-(5-phosphoribitylamino)uracil, 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5'-phosphate

Citations: [Graupner02, Mashhadi08]

Chemical Formula: C9H15N4O9P

Molecular Weight: 354.21 Daltons

Monoisotopic Molecular Weight: 356.0733146754 Daltons

5-amino-6-(5-phospho-D-ribitylamino)uracil compound structure

SMILES: C(NC1(NC(NC(=O)C(N)=1)=O))C(O)C(O)C(O)COP([O-])(=O)[O-]

InChI: InChI=1S/C9H17N4O9P/c10-5-7(12-9(18)13-8(5)17)11-1-3(14)6(16)4(15)2-22-23(19,20)21/h3-4,6,14-16H,1-2,10H2,(H2,19,20,21)(H3,11,12,13,17,18)/p-2/t3-,4+,6-/m0/s1


Unification Links: ChEBI:58421, HMDB:HMDB03841, IAF1260:43851, KEGG:C04454, PubChem:45266638

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -260.70145Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

flavin biosynthesis I (bacteria and plants) , flavin biosynthesis II (archaea) , flavin biosynthesis III (fungi) :
5-amino-6-(5-phospho-D-ribitylamino)uracil + H2O → 5-amino-6-(D-ribitylamino)uracil + phosphate

Reactions known to produce the compound:

flavin biosynthesis I (bacteria and plants) :
5-amino-6-(5-phospho-D-ribitylamino)uracil + NADP+ ← 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH + H+

flavin biosynthesis II (archaea) , flavin biosynthesis III (fungi) :
2,5-diamino-6-(5-phospho-D-ribitylamino)pyrimidin-4(3H)-one + H+ + H2O → 5-amino-6-(5-phospho-D-ribitylamino)uracil + ammonium

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


Graupner02: Graupner M, Xu H, White RH (2002). "The pyrimidine nucleotide reductase step in riboflavin and F(420) biosynthesis in archaea proceeds by the eukaryotic route to riboflavin." J Bacteriol 184(7);1952-7. PMID: 11889103

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

Mashhadi08: Mashhadi Z, Zhang H, Xu H, White RH (2008). "Identification and characterization of an archaeon-specific riboflavin kinase." J Bacteriol 190(7);2615-8. PMID: 18245297

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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