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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

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


a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

Not in pathways:
an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

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

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

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

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

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]


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
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, biocyc14.