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MetaCyc Compound: 6-pyruvoyl tetrahydropterin

Synonyms: 6-pyruvoyl-5,6,7,8-tetrahydropterin, 6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin, pyruvoyl-H4-pterin, PPH4

Superclasses: an organic heterocyclic compoundan organic heterobicyclic compounda pteridinea 5,6,7,8-tetrahydropteridinea tetrahydropterin
an organic heterocyclic compoundan organic heterobicyclic compounda pteridinea pterina tetrahydropterin
an organic heterocyclic compoundan organonitrogen heterocyclic compounda pteridinea 5,6,7,8-tetrahydropteridinea tetrahydropterin
an organic heterocyclic compoundan organonitrogen heterocyclic compounda pteridinea pterina tetrahydropterin

Chemical Formula: C9H11N5O3

Molecular Weight: 237.22 Daltons

Monoisotopic Molecular Weight: 237.0861892454 Daltons

6-pyruvoyl tetrahydropterin compound structure

SMILES: CC(=O)C(=O)[CH]1(CNC2(N=C(N)NC(=O)C(N1)=2))

InChI: InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)/t4-/m1/s1

InChIKey: InChIKey=WBJZXBUVECZHCE-SCSAIBSYSA-N

Unification Links: ChEBI:17804, ChemSpider:114280, HMDB:HMDB01195, KEGG:C03684, MetaboLights:MTBLC17804, PubChem:644062

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 60.35232Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

drosopterin and aurodrosopterin biosynthesis :
2-amino-6-acetyl-3,7,8,9-tetrahydro-3H-pyrimido[4,5-b][1,4]diazepin-4-one + glutathione disulfide + H2O ← 6-pyruvoyl tetrahydropterin + 2 glutathione
6-pyruvoyl tetrahydropterin → 7,8-dihydropterin

tetrahydrobiopterin biosynthesis I :
L-erythro-5,6,7,8-tetrahydrobiopterin + 2 NADP+6-pyruvoyl tetrahydropterin + 2 NADPH + 2 H+

tetrahydrobiopterin biosynthesis II :
6-lactoyl-5,6,7,8-tetrahydropterin + NADP+6-pyruvoyl tetrahydropterin + NADPH + H+

tetrahydrobiopterin biosynthesis III :
L-threo-5,6,7,8-tetrahydrobiopterin + 2 NADP+6-pyruvoyl tetrahydropterin + 2 NADPH + 2 H+

Reactions known to produce the compound:

drosopterin and aurodrosopterin biosynthesis , tetrahydrobiopterin biosynthesis I , tetrahydrobiopterin biosynthesis II , tetrahydrobiopterin biosynthesis III :
7,8-dihydroneopterin 3'-triphosphate → 6-pyruvoyl tetrahydropterin + PPPi + H+

In Reactions of unknown directionality:

Not in pathways:
a 5,6,7,8-tetrahydropteridine + NAD(P)+ = a 6,7-dihydropteridine + NAD(P)H + H+

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: benzoate 4-monooxygenase

This compound has been characterized as an alternative substrate of the following enzymes: 6-carboxy-5,6,7,8-tetrahydropterin synthase


References

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


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
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