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MetaCyc Compound: 5-phospho-α-D-ribose 1-diphosphate

Abbrev Name: PRPP

Synonyms: PRPP, 5-phosphoribosyl 1-pyrophosphate, 5-phosphoribosyl diphosphate, 5-phosphoribosyl-1-PP, 5-phosphoribosyl-PP, 5-phosphoribosyl-1-pyrophosphate, 5-phosphoribosylpyrophosphate, phosphoribosylpyrophosphate, 5-phospho-ribosyl-pyrophosphate, α-D-5-phosphoribosylPP, α-D-5-P-RibosylPP

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate

Chemical Formula: C5H8O14P3

Molecular Weight: 385.03 Daltons

Monoisotopic Molecular Weight: 389.9518146567 Daltons

5-phospho-α-D-ribose 1-diphosphate compound structure

SMILES: C(OP(=O)([O-])[O-])C1(OC(OP([O-])(=O)OP([O-])(=O)[O-])C(O)C(O)1)

InChI: InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/p-5/t2-,3-,4-,5-/m1/s1

InChIKey: InChIKey=PQGCEDQWHSBAJP-TXICZTDVSA-I

Unification Links: CAS:13270-65-0 , ChEBI:58017 , ChemSpider:20171339 , HMDB:HMDB00280 , IAF1260:33926 , KEGG:C00119 , MetaboLights:MTBLC58017 , PubChem:20848918

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -740.25256 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

adenine and adenosine salvage I , adenine and adenosine salvage II , adenine and adenosine salvage IV :
AMP + diphosphate ← adenine + 5-phospho-α-D-ribose 1-diphosphate

mycolyl-arabinogalactan-peptidoglycan complex biosynthesis :
5-phospho-α-D-ribose 1-diphosphate + trans,octacis-decaprenyl phosphate + H+trans,octacis-decaprenylphospho-β-D-ribofuranose 5-phosphate + diphosphate

NAD biosynthesis from 2-amino-3-carboxymuconate semialdehyde , NAD biosynthesis I (from aspartate) , nicotine biosynthesis , superpathway of nicotine biosynthesis :
β-nicotinate D-ribonucleotide + CO2 + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + quinolinate + 2 H+

NAD biosynthesis III :
β-nicotinamide D-ribonucleotide + diphosphate ← nicotinamide + 5-phospho-α-D-ribose 1-diphosphate + H+

NAD salvage pathway I , pyridine nucleotide cycling (plants) :
nicotinate + 5-phospho-α-D-ribose 1-diphosphate + ATP + H2O → β-nicotinate D-ribonucleotide + ADP + diphosphate + phosphate

paromomycin biosynthesis :
paromamine + 5-phospho-α-D-ribose 1-diphosphate → 5''-phosphoribosylparomamine + diphosphate

pyrimidine nucleobases salvage I :
UMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + uracil

ribostamycin biosynthesis :
neamine + 5-phospho-α-D-ribose 1-diphosphate → 5''-phosphoribostamycin + diphosphate

tetrahydromethanopterin biosynthesis :
4-hydroxybenzoate + 5-phospho-α-D-ribose 1-diphosphate + H+ → 4-(β-D-ribofuranosyl)hydroxybenzene 5'-phosphate + CO2 + diphosphate
[1-(2-amino-7-methyl-4-oxo-7,8-dihydro-3H-pteridin-6-yl)]ethyl-(4-aminophenyl)-1-deoxy-D-ribitol + 5-phospho-α-D-ribose 1-diphosphate → [1-(2-amino-7-methyl-4-oxo-7,8-dihydro-3H-pteridin-6-yl)]ethyl-(4-aminophenyl)-1-deoxy-5-[1-α -D- ribofuranosyl 5-phosphate]-D-ribitol + diphosphate

toyocamycin biosynthesis :
5-phospho-α-D-ribose-1-preQ0 + diphosphate ← preQ0 + 5-phospho-α-D-ribose 1-diphosphate

xanthine and xanthosine salvage :
XMP + diphosphate ← xanthine + 5-phospho-α-D-ribose 1-diphosphate

Not in pathways:
5-phospho-α-D-ribose 1-diphosphate + 4-imidazoleacetate + ATP → 1-(5-phosphoribosyl)imidazole-4-acetate + ADP + phosphate + diphosphate

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to both consume and produce the compound:

4-amino-2-methyl-5-phosphomethylpyrimidine biosynthesis (yeast) , 5-aminoimidazole ribonucleotide biosynthesis I , 5-aminoimidazole ribonucleotide biosynthesis II , superpathway of 5-aminoimidazole ribonucleotide biosynthesis :
5-phospho-β-D-ribosylamine + L-glutamate + diphosphate ↔ 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O

adenine and adenosine salvage III , adenine and adenosine salvage IV :
IMP + diphosphate ↔ hypoxanthine + 5-phospho-α-D-ribose 1-diphosphate

adenosine nucleotides degradation IV , PRPP biosynthesis II :
α-D-ribose 1,5-bisphosphate + ATP ↔ 5-phospho-α-D-ribose 1-diphosphate + ADP

guanine and guanosine salvage , guanine and guanosine salvage II :
GMP + diphosphate ↔ guanine + 5-phospho-α-D-ribose 1-diphosphate

L-histidine biosynthesis :
1-(5-phospho-β-D-ribosyl)-ATP + diphosphate ↔ ATP + 5-phospho-α-D-ribose 1-diphosphate + H+

L-tryptophan biosynthesis :
N-(5-phosphoribosyl)-anthranilate + diphosphate ↔ anthranilate + 5-phospho-α-D-ribose 1-diphosphate

PRPP biosynthesis I :
D-ribose 5-phosphate + ATP ↔ 5-phospho-α-D-ribose 1-diphosphate + AMP + H+

UMP biosynthesis :
orotidine 5'-phosphate + diphosphate ↔ 5-phospho-α-D-ribose 1-diphosphate + orotate

In Reactions of unknown directionality:

Not in pathways:
a 2,4-dioxotetrahydropyrimidine D-ribonucleotide + diphosphate = 5,6-dihydrouracil + 5-phospho-α-D-ribose 1-diphosphate
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + diphosphate = 5-amino-4-imidazolecarboxyamide + 5-phospho-α-D-ribose 1-diphosphate
5-phospho-α-D-ribose 1-diphosphate + H2O = α-D-ribose 1,5-bisphosphate + phosphate + H+

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

This compound has been characterized as an alternative substrate of the following enzymes: thiamin monophosphate phosphatase


References

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


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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
Page generated by SRI International Pathway Tools version 19.0 on Sat Jul 4, 2015, biocyc11.