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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 22:57:04 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhosphoribosyl pyrophosphate
DescriptionPhosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia).
  1. 5-Phospho-a-D-ribose-1-diphosphate
  2. 5-Phospho-a-D-ribosyl pyrophosphate
  3. 5-Phospho-alpha-D-ribose 1-diphosphate
  4. 5-Phospho-alpha-D-ribose-1-diphosphate
  5. 5-Phospho-alpha-D-ribosyl pyrophosphate
  6. 5-Phospho-alpha-D-riobse 1-diphosphate
  7. 5-Phospho-alpha-delta-ribose 1-diphosphate
  8. 5-Phospho-alpha-delta-ribose-1-diphosphate
  9. 5-Phospho-alpha-delta-ribosyl pyrophosphate
  10. 5-Phosphoribose 1-pyrophosphate
  11. 5-Phosphoribosyl 1-diphosphate
  12. 5-Phosphoribosyl a-1-pyrophosphate
  13. 5-Phosphoribosyl-1-pyrophosphate
  14. 5-Phosphorylribose 1-a-diphosphate
  15. 5-Phosphorylribose 1-alpha-diphosphate
  16. 5-Phosphorylribose 1-pyrophosphate
  17. 5-Phosphorylribosyl 1-pyrophosphate
  18. a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  19. a-D-5-Phosphoribosyl 1-pyrophosphate
  20. a-D-Ribofuranose 5-phosphate 1-pyrophosphate
  21. a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  22. alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  23. alpha-D-5-Phosphoribosyl 1-pyrophosphate
  24. alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate
  25. alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
  26. alpha-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
  27. alpha-delta-5-Phosphoribosyl 1-pyrophosphate
  28. alpha-delta-Ribofuranose 5-phosphate 1-pyrophosphate
  29. Phosphoribosyl pyrophosphate
  30. Phosphoribosyl-1-pyrophosphate
  31. Phosphoribosyl-pyrophosphate
  32. Phosphoribosylpyrophosphorate
  33. Phosphoribosylpyrophosphoric acid
  34. PP-Ribose-P
  35. PRib-PP
  36. PRPP
Chemical FormulaC5H13O14P3
Average Molecular Weight390.0696
Monoisotopic Molecular Weight389.95181466
IUPAC Name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namephosphoribosylpyrophosphate
CAS Registry Number7540-64-9
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharide phosphates
Alternative Parents
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility11.6 mg/mLALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.74 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m3·mol-1ChemAxon
Polarizability27.45 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location
  • Erythrocyte
  • Fibroblasts
Pentose Phosphate PathwaySMP00031map00030
Purine MetabolismSMP00050map00230
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
BloodDetected and Quantified5.72 +/- 0.86 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified4.9 +/- 2.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021928
KNApSAcK IDNot Available
Chemspider ID7062
KEGG Compound IDC00119
BiGG ID33926
Wikipedia LinkPhosphoribosyl pyrophosphate
NuGOwiki LinkHMDB00280
Metagene LinkHMDB00280
PubChem Compound7339
ChEBI ID17111
Synthesis ReferenceGross, 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 (1983), 105(25), 7428-35.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Snyder FF, Dyer C, Seegmiller JE, Goldblum RM, Mills GC, Schmalstieg FC: Substrate inhibition of adenosine phosphorylation in adenosine deaminase deficiency and adenosine-mediated inhibition of PP-ribose-P dependent nucleotide synthesis in hypoxanthine phosphoribosyltransferase deficient erythrocytes. J Inherit Metab Dis. 1988;11(2):174-83. [2459496 ]
  2. Gordon RB, Keough DT, Emmerson BT: HPRT-deficiency associated with normal PRPP concentration and APRT activity. J Inherit Metab Dis. 1987;10(1):82-8. [2437388 ]
  3. Nishida Y, Akaoka I, Nishizawa T, Maruki M, Maruki K: Synthesis and concentration of 5-phosphoribosyl-1-pyrophosphate in erythrocytes from patients with Down's syndrome. Ann Rheum Dis. 1977 Jun;36(3):261-3. [141914 ]
  4. Ghitis J, Schreiber C, Waxman S: Phosphate-induced phosphoribosylpyrophosphate elevations to assess deranged folate and purine nucleotide metabolism. Proc Soc Exp Biol Med. 1987 Oct;186(1):90-5. [2442765 ]
  5. Yamaoka T, Yano M, Kondo M, Sasaki H, Hino S, Katashima R, Moritani M, Itakura M: Feedback inhibition of amidophosphoribosyltransferase regulates the rate of cell growth via purine nucleotide, DNA, and protein syntheses. J Biol Chem. 2001 Jun 15;276(24):21285-91. Epub 2001 Apr 4. [11290738 ]
  6. Blinov MN, Kamyshentsev MV, Luganova IS, Filanovskaia LI, Filippova VN: [Phosphoribosyl pyrophosphate and its metabolic enzymes in the erythrocytes in certain forms of anemia] Vopr Med Khim. 1976 Jul-Aug;22(4):456-62. [194412 ]
  7. Micheli V, Taddeo A: [Spectrophotometric assay of 5-phosphoribosyl-1-pyrophosphate synthetase (PRPP) in erythrocyte lysate (author's transl)] Quad Sclavo Diagn. 1981 Jun;17(2):209-15. [6267652 ]
  8. Sakuma R, Nishina T, Yamanaka H, Kamatani N, Nishioka K, Maeda M, Tsuji A: Phosphoribosylpyrophosphate synthetase in human erythrocytes: assay and kinetic studies using high-performance liquid chromatography. Clin Chim Acta. 1991 Dec 16;203(2-3):143-52. [1663846 ]
  9. Zoref-Shani E, Feinstein S, Frishberg Y, Bromberg Y, Sperling O: Kelley-Seegmiller syndrome due to a unique variant of hypoxanthine-guanine phosphoribosyltransferase: reduced affinity for 5-phosphoribosyl-1-pyrophosphate manifested only at low, physiological substrate concentrations. Biochim Biophys Acta. 2000 Feb 21;1500(2):197-203. [10657589 ]
  10. Sperling O, Boer P, Brosh S, Elazar E, Szeinberg A, de Vries A: Normal activity of metabolic pathways involved in the formation and utilization of phosphoribosylpyrophosphate in erythrocytes of patients with primary metabolic gout. Nutr Metab. 1975;18(4):217-23. [172821 ]
  11. Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes] Lab Delo. 1977;(12):724-5. [75318 ]
  12. Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6. [193371 ]
  13. Becker MA, Losman MJ, Itkin P, Simkin PA: Gout with superactive phosphoribosylpyrophosphate synthetase due to increased enzyme catalytic rate. J Lab Clin Med. 1982 Apr;99(4):495-511. [6174658 ]
  14. Tax WJ, Veerkamp JH: A simple and sensitive method for estimating the concentration and synthesis of 5-phosphoribosyl 1-pyrophosphate in red blood cells. Clin Chim Acta. 1977 Jul 15;78(2):209-16. [195752 ]
  15. MacDermot KD, Allsop J, Watts RW: The rate of purine synthesis de nova in blood mononuclear cells in vitro from patients with familial hyperuricaemic nephropathy. Clin Sci (Lond). 1984 Aug;67(2):249-58. [6744792 ]
  16. Emmerson BT, Gordon RB, Thompson L: Adenine phosphoribosyltransferase deficiency: its inheritance and occurrence in a female with gout and renal disease. Aust N Z J Med. 1975 Oct;5(5):440-6. [1061547 ]
  17. Zerez CR, Lachant NA, Tanaka KR: Decreased erythrocyte phosphoribosylpyrophosphate synthetase activity and impaired formation in thalassemia minor: a mechanism for decreased adenine nucleotide content. J Lab Clin Med. 1989 Jul;114(1):43-50. [2544652 ]
  18. Rylance HJ, Wallace RC, Nuki G: A method for the determination of 5-phosphoribosyl 1-pyrophosphate concentrations in erythrocytes using high-performance liquid chromatography. Anal Biochem. 1987 Feb 1;160(2):337-41. [2437821 ]
  19. Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50. [2445472 ]
  20. Lachant NA, Zerez CR, Tanaka KR: Pyrimidine nucleotides impair phosphoribosylpyrophosphate (PRPP) synthetase subunit aggregation by sequestering magnesium. A mechanism for the decreased PRPP synthetase activity in hereditary erythrocyte pyrimidine 5'-nucleotidase deficiency. Biochim Biophys Acta. 1989 Jan 19;994(1):81-8. [2535789 ]


General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
5-Phosphoribosylamine + Pyrophosphate + L-Glutamic acid → L-Glutamine + Phosphoribosyl pyrophosphate + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
Uniprot ID:
Molecular weight:
nicotinate beta-D-ribonucleotide + Pyrophosphate + CO(2) → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
nicotinate beta-D-ribonucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
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:
Uniprot ID:
Molecular weight:
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
Uniprot ID:
Molecular weight:
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
Xanthylic acid + Pyrophosphate → Xanthine + Phosphoribosyl pyrophosphatedetails
Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
6-Methylmercaptopurine + Phosphoribosyl pyrophosphate → 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphatedetails
Thioguanine + Phosphoribosyl pyrophosphate → 6-Thioguanosine monophosphate + Pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
Uniprot ID:
Molecular weight:
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
Uniprot ID:
Molecular weight:
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
Uniprot ID:
Molecular weight:
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Orotidylic acid + Pyrophosphate → Orotic acid + Phosphoribosyl pyrophosphatedetails
Fluorouracil + Phosphoribosyl pyrophosphate → 5-Fluorouridine monophosphate + Pyrophosphatedetails
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to yield nicotinamide mononucleotide, an intermediate in the biosynthesis of NAD. It is the rate limiting component in the mammalian NAD biosynthesis pathway (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
beta-nicotinamide D-ribonucleotide + Pyrophosphate → Niacinamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the conversion of nicotinic acid (NA) to NA mononucleotide (NaMN). Essential for NA to increase cellular NAD levels and prevent oxidative stress of the cells.
Gene Name:
Uniprot ID:
Molecular weight:
nicotinate beta-D-ribonucleotide + Pyrophosphate → Nicotinic acid + Phosphoribosyl pyrophosphatedetails
General function:
Involved in nucleoside metabolic process
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
Uridine 5'-monophosphate + Pyrophosphate → Uracil + Phosphoribosyl pyrophosphatedetails