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Identification
YMDB IDYMDB00402
NamePhosphoribosyl pyrophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphoribosyl pyrophosphate, also known as PRPP or prib-PP, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Phosphoribosyl pyrophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoribosyl pyrophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 5-Phospho-a-D-ribose-1-diphosphate
  • 5-Phospho-a-D-ribosyl pyrophosphate
  • 5-Phospho-alpha-D-ribose 1-diphosphate
  • 5-Phospho-alpha-D-ribose-1-diphosphate
  • 5-Phospho-alpha-D-ribosyl pyrophosphate
  • 5-phospho-alpha-D-riobse 1-diphosphate
  • 5-Phospho-alpha-delta-ribose 1-diphosphate
  • 5-Phospho-alpha-delta-ribose-1-diphosphate
  • 5-Phospho-alpha-delta-ribosyl pyrophosphate
  • 5-Phosphoribose 1-pyrophosphate
  • 5-Phosphoribosyl 1-diphosphate
  • 5-Phosphoribosyl a-1-pyrophosphate
  • 5-Phosphoribosyl-1-pyrophosphate
  • 5-Phosphorylribose 1-a-diphosphate
  • 5-Phosphorylribose 1-alpha-diphosphate
  • 5-Phosphorylribose 1-pyrophosphate
  • 5-Phosphorylribosyl 1-pyrophosphate
  • a-D-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  • a-D-5-Phosphoribosyl 1-pyrophosphate
  • a-D-Ribofuranose 5-phosphate 1-pyrophosphate
  • a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  • alpha-D-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  • alpha-D-5-Phosphoribosyl 1-pyrophosphate
  • alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate
  • alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  • alpha-delta-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  • alpha-delta-5-Phosphoribosyl 1-pyrophosphate
  • alpha-delta-Ribofuranose 5-phosphate 1-pyrophosphate
  • Phosphoribosyl pyrophosphate
  • Phosphoribosyl pyrophosphic acid
  • Phosphoribosyl-1-pyrophosphate
  • Phosphoribosyl-pyrophosphate
  • Phosphoribosylpyrophosphorate
  • Phosphoribosylpyrophosphoric acid
  • PP-Ribose-P
  • PRib-PP
  • PRPP
  • 5-Phosphoribosyl 1-pyrophosphate
  • 5-Phosphoribosyl diphosphate
  • alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  • ALPHA-PHOSPHORIBOSYLPYROphosphORIC ACID
  • Phosphoribosylpyrophosphate
  • 5-Phospho-a-D-ribose 1-diphosphate
  • 5-Phospho-a-D-ribose 1-diphosphoric acid
  • 5-Phospho-alpha-D-ribose 1-diphosphoric acid
  • 5-Phospho-α-D-ribose 1-diphosphate
  • 5-Phospho-α-D-ribose 1-diphosphoric acid
  • 5-Phosphoribosyl 1-pyrophosphoric acid
  • 5-Phosphoribosyl diphosphoric acid
  • a-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  • a-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
  • alpha-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
  • Α-D-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  • Α-D-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
  • a-PHOSPHORIBOSYLPYROphosphate
  • a-PHOSPHORIBOSYLPYROphosphoric acid
  • alpha-PHOSPHORIBOSYLPYROphosphate
  • Α-phosphoribosylpyrophosphate
  • Α-phosphoribosylpyrophosphoric acid
  • Phosphoribosyl pyrophosphoric acid
  • Pyrophosphate, phosphoribosyl
CAS number7540-64-9
WeightAverage: 390.0696
Monoisotopic: 389.95181466
InChI KeyPQGCEDQWHSBAJP-TXICZTDVSA-N
InChIInChI=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)/t2-,3-,4-,5-/m1/s1
IUPAC Name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional IUPAC Namephosphoribosylpyrophosphate
Chemical FormulaC5H13O14P3
SMILES[H]O[C@@]1([H])[C@@]([H])(OP(=O)(O[H])OP(=O)(O[H])O[H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.6 g/LALOGPS
logP-0.74ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m³·mol⁻¹ChemAxon
Polarizability27.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
Pentose phosphate pathwayec00030 Map00030
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Purine metabolismec00230 Map00230
Pyrimidine metabolismec00240 Map00240
SMPDB Reactions
D-Ribose 5-phosphate + Adenosine triphosphateAdenosine monophosphate + hydron + Phosphoribosyl pyrophosphate
Phosphoribosyl pyrophosphate + Adenosine triphosphate + hydronPyrophosphate + 1-(5-phosphoribosyl)-5'-AMP
Phosphoribosyl pyrophosphate + Adenosine triphosphate + hydronPyrophosphate + 1-(5-phosphoribosyl)-ATP
Quinolinic acid + hydron + Phosphoribosyl pyrophosphatePyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
water + Adenosine triphosphate + Phosphoribosyl pyrophosphate + Nicotinic acidNicotinic acid mononucleotide + Pyrophosphate + ADP + phosphate
KEGG Reactions
Phosphoribosyl pyrophosphate + AdenineAdenosine monophosphate + Pyrophosphate
2-Aminobenzoic acid + Phosphoribosyl pyrophosphatePyrophosphate + N-(5-phospho-beta-D-ribosyl)anthranilic acid
Adenosine triphosphate + Phosphoribosyl pyrophosphatePyrophosphate + 5-phosphoribosyl-ATP
water + L-Glutamine + Phosphoribosyl pyrophosphatePyrophosphate + L-Glutamic acid + 5-Phosphoribosylamine
Phosphoribosyl pyrophosphate + GuaninePyrophosphate + Guanosine monophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • de Figueiredo, L. F., Gossmann, T. I., Ziegler, M., Schuster, S. (2011). "Pathway Analysis of NAD+ metabolism." Biochem J :.21729004
Synthesis Reference:Gross, Akiva; Abril, Obsidiana; Lewis, Jerome M.; Geresh, Shimona; Whitesides, George M. Practical synthesis of 5-phospho-D-ribosyl a-1-pyrophosphate (PRPP): enzymatic routes from ribose 5-phosphate or ribose. Journal of the American Chemical Society (
External Links:
ResourceLink
CHEBI ID17111
HMDB IDHMDB00280
Pubchem Compound ID7339
Kegg IDC00119
ChemSpider ID7062
FOODB IDFDB021928
WikipediaPhosphoribosyl_pyrophosphate
BioCyc IDPRPP

Enzymes

General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O
Gene Name:
ADE4
Uniprot ID:
P04046
Molecular weight:
56718.89844
Reactions
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate → L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O.
General function:
Involved in orotate phosphoribosyltransferase activity
Specific function:
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:
URA5
Uniprot ID:
P13298
Molecular weight:
24664.19922
Reactions
Orotidine 5'-phosphate + diphosphate → orotate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in orotate phosphoribosyltransferase activity
Specific function:
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:
URA10
Uniprot ID:
P30402
Molecular weight:
24810.30078
Reactions
Orotidine 5'-phosphate + diphosphate → orotate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:
TRP4
Uniprot ID:
P07285
Molecular weight:
41374.0
Reactions
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate → anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA)
Gene Name:
BNA6
Uniprot ID:
P43619
Molecular weight:
32364.69922
Reactions
Nicotinate D-ribonucleotide + diphosphate + CO(2) → pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
5-phosphoribose 1-diphosphate synthase involved in nucleotide, histidine, and tryptophan biosynthesis. Active in heteromultimeric complexes with other 5-phosphoribose 1- diphosphate synthases (PRS2, PRS3, PRS4 and PRS5)
Gene Name:
PRS5
Uniprot ID:
Q12265
Molecular weight:
53504.19922
Reactions
ATP + D-ribose 5-phosphate → AMP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
5-phosphoribose 1-diphosphate synthase involved in nucleotide, histidine, and tryptophan biosynthesis. Active in heteromultimeric complexes with other 5-phosphoribose 1- diphosphate synthases (PRS2, PRS3, PRS4 and PRS5)
Gene Name:
PRS2
Uniprot ID:
P38620
Molecular weight:
34764.60156
Reactions
ATP + D-ribose 5-phosphate → AMP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
Gene Name:
APT1
Uniprot ID:
P49435
Molecular weight:
20586.59961
Reactions
AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
5-phosphoribose 1-diphosphate synthase involved in nucleotide, histidine, and tryptophan biosynthesis. Active in heteromultimeric complexes with other 5-phosphoribose 1- diphosphate synthases (PRS2, PRS3, PRS4 and PRS5)
Gene Name:
PRS1
Uniprot ID:
P32895
Molecular weight:
47047.0
Reactions
ATP + D-ribose 5-phosphate → AMP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis. May lack catalytic activity
Gene Name:
APT2
Uniprot ID:
P36973
Molecular weight:
19999.80078
Reactions
AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
5-phosphoribose 1-diphosphate synthase involved in nucleotide, histidine, and tryptophan biosynthesis. Active in heteromultimeric complexes with other 5-phosphoribose 1- diphosphate synthases (PRS2, PRS3, PRS4 and PRS5)
Gene Name:
PRS3
Uniprot ID:
P38689
Molecular weight:
35123.30078
Reactions
ATP + D-ribose 5-phosphate → AMP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in ATP phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of ATP and 5-phosphoribose 1- diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems to be controlled primarily by regulation of the enzymatic activity
Gene Name:
HIS1
Uniprot ID:
P00498
Molecular weight:
32266.09961
Reactions
1-(5-phospho-D-ribosyl)-ATP + diphosphate → ATP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Essential for growth under anaerobic conditions
Gene Name:
NPT1
Uniprot ID:
P39683
Molecular weight:
49018.19922
Reactions
Nicotinate D-ribonucleotide + diphosphate → nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
IMP + diphosphate = hypoxanthine + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:
HPT1
Uniprot ID:
Q04178
Molecular weight:
25190.5
Reactions
IMP + diphosphate → hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
GMP + diphosphate → guanine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
May act as a xanthine phosphoribosyltransferase involved in the synthesis of purine nucleotides. Such activity is however unclear in vivo
Gene Name:
XPT1
Uniprot ID:
P47165
Molecular weight:
23671.0
Reactions
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
Gene Name:
FUR1
Uniprot ID:
P18562
Molecular weight:
24594.19922
Reactions
UMP + diphosphate → uracil + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
5-phosphoribose 1-diphosphate synthase involved in nucleotide, histidine, and tryptophan biosynthesis. Active in heteromultimeric complexes with other 5-phosphoribose 1- diphosphate synthases (PRS2, PRS3, PRS4 and PRS5)
Gene Name:
PRS4
Uniprot ID:
P38063
Molecular weight:
35845.69922
Reactions
ATP + D-ribose 5-phosphate → AMP + 5-phospho-alpha-D-ribose 1-diphosphate.