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Human Metabolome Database Version 3.5

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Showing metabocard for Phosphoribosyl pyrophosphate (HMDB00280)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:14 -0700
HMDB ID HMDB00280
Secondary Accession Numbers None
Metabolite Identification
Common Name Phosphoribosyl pyrophosphate
Description Phosphoribosyl 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).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  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 Formula C5H13O14P3
Average Molecular Weight 390.0696
Monoisotopic Molecular Weight 389.95181466
IUPAC Name {[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number 7540-64-9
SMILES O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI Identifier 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)/t2-,3-,4-,5-/m1/s1
InChI Key PQGCEDQWHSBAJP-TXICZTDVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
Other Descriptors
  • 5-O-phosphono-D-ribofuranosyl diphosphate(ChEBI)
  • Aliphatic Heteromonocyclic Compounds
  • Monosaccharide Phosphates
  • Organic Pyrophosphates
Substituents
  • 1,2 Diol
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Pentoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11.6 g/L ALOGPS
LogP -0.74 ALOGPS
LogP -3 ChemAxon
LogS -1.53 ALOGPS
pKa (strongest acidic) 1.09 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 229.74 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 62.58 ChemAxon
Polarizability 27.11 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Erythrocyte
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Purine Metabolism SMP00050 map00230 Link_out
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
5.72 +/- 0.86 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
4.9 +/- 2.1 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021928
KNApSAcK ID Not Available
Chemspider ID 7062 Link_out
KEGG Compound ID C00119 Link_out
BioCyc ID PRPP Link_out
BiGG ID 33926 Link_out
Wikipedia Link Phosphoribosyl pyrophosphate Link_out
NuGOwiki Link HMDB00280 Link_out
Metagene Link HMDB00280 Link_out
METLIN ID 5274 Link_out
PubChem Compound 7339 Link_out
PDB ID PRP Link_out
ChEBI ID 17111 Link_out
References
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 (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. Pubmed: 2459496 Link_out
  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. Pubmed: 2437388 Link_out
  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. Pubmed: 141914 Link_out
  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. Pubmed: 2442765 Link_out
  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. Pubmed: 11290738 Link_out
  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. Pubmed: 194412 Link_out
  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. Pubmed: 6267652 Link_out
  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. Pubmed: 1663846 Link_out
  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. Pubmed: 10657589 Link_out
  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. Pubmed: 172821 Link_out
  11. Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes] Lab Delo. 1977;(12):724-5. Pubmed: 75318 Link_out
  12. Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6. Pubmed: 193371 Link_out
  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. Pubmed: 6174658 Link_out
  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. Pubmed: 195752 Link_out
  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. Pubmed: 6744792 Link_out
  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. Pubmed: 1061547 Link_out
  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. Pubmed: 2544652 Link_out
  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. Pubmed: 2437821 Link_out
  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. Pubmed: 2445472 Link_out
  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. Pubmed: 2535789 Link_out
Enzymes
Name: Nicotinate-nucleotide pyrophosphorylase [carboxylating]
Reactions:
  • nicotinate D-ribonucleotide + diphosphate + CO2 = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R03348]
Gene Name: QPRT
Uniprot ID: Q15274 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenine phosphoribosyltransferase
Reactions:
  • AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R00190]
Gene Name: APRT
Uniprot ID: P07741 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hypoxanthine-guanine phosphoribosyltransferase
Reactions:
  • IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01132]
Gene Name: HPRT1
Uniprot ID: P00492 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribose-phosphate pyrophosphokinase 3
Reactions:
  • ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01049]
Gene Name: PRPS1L1
Uniprot ID: P21108 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribose-phosphate pyrophosphokinase 1
Reactions:
  • ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01049]
Gene Name: PRPS1
Uniprot ID: P60891 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribose-phosphate pyrophosphokinase 2
Reactions:
  • ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01049]
Gene Name: PRPS2
Uniprot ID: P11908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nicotinamide phosphoribosyltransferase
Reactions:
  • nicotinamide D-ribonucleotide + diphosphate = nicotinamide + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01271]
Gene Name: NAMPT
Uniprot ID: P43490 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA