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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-03-12 18:26:04 UTC |
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| HMDB ID | HMDB0000280 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Phosphoribosyl pyrophosphate |
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| Description | Phosphoribosyl 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. Within humans, phosphoribosyl pyrophosphate participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in adenosine deaminase deficiency. Phosphoribosyl pyrophosphate is a pentosephosphate and it is 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 5-Phospho-alpha-D-ribose 1-diphosphate | ChEBI | | 5-Phosphoribosyl 1-pyrophosphate | ChEBI | | 5-Phosphoribosyl diphosphate | ChEBI | | alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) | ChEBI | | alpha-Phosphoribosylpyrophosphoric acid | ChEBI | | Phosphoribosylpyrophosphate | ChEBI | | PRib-PP | ChEBI | | PRPP | ChEBI | | 5-Phospho-a-D-ribose 1-diphosphate | Generator | | 5-Phospho-a-D-ribose 1-diphosphoric acid | Generator | | 5-Phospho-alpha-D-ribose 1-diphosphoric acid | Generator | | 5-Phospho-α-D-ribose 1-diphosphate | Generator | | 5-Phospho-α-D-ribose 1-diphosphoric acid | Generator | | Phosphoribosyl pyrophosphoric acid | Generator | | 5-Phosphoribosyl 1-pyrophosphoric acid | Generator | | 5-Phosphoribosyl diphosphoric acid | Generator | | a-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) | Generator | | a-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) | Generator | | alpha-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) | Generator | | α-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) | Generator | | α-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) | Generator | | a-Phosphoribosylpyrophosphate | Generator | | a-Phosphoribosylpyrophosphoric acid | Generator | | alpha-Phosphoribosylpyrophosphate | Generator | | α-Phosphoribosylpyrophosphate | Generator | | α-Phosphoribosylpyrophosphoric acid | Generator | | Phosphoribosylpyrophosphoric acid | Generator | | 5-Phospho-a-D-ribose-1-diphosphate | HMDB | | 5-Phospho-a-D-ribosyl pyrophosphate | HMDB | | 5-Phospho-alpha-D-ribose-1-diphosphate | HMDB | | 5-Phospho-alpha-D-ribosyl pyrophosphate | HMDB | | 5-Phosphoribose 1-pyrophosphate | HMDB | | 5-Phosphoribosyl 1-diphosphate | HMDB | | 5-Phosphoribosyl a-1-pyrophosphate | HMDB | | 5-Phosphoribosyl-1-pyrophosphate | HMDB | | 5-Phosphorylribose 1-a-diphosphate | HMDB | | 5-Phosphorylribose 1-alpha-diphosphate | HMDB | | 5-Phosphorylribose 1-pyrophosphate | HMDB | | 5-Phosphorylribosyl 1-pyrophosphate | HMDB | | a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose | HMDB | | a-D-5-Phosphoribosyl 1-pyrophosphate | HMDB | | a-D-Ribofuranose 5-phosphate 1-pyrophosphate | HMDB | | a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) | HMDB | | alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose | HMDB | | alpha-D-5-Phosphoribosyl 1-pyrophosphate | HMDB | | alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate | HMDB | | alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) | HMDB | | Phosphoribosyl-1-pyrophosphate | HMDB | | Phosphoribosyl-pyrophosphate | HMDB | | Phosphoribosylpyrophosphorate | HMDB | | PP-Ribose-P | HMDB | | Pyrophosphate, phosphoribosyl | MeSH, HMDB | | 5-Phospho-α-D-ribose-1-diphosphate | HMDB | | 5-Phospho-α-D-ribosyl pyrophosphate | HMDB | | 5-Phosphoribosyl alpha-1-pyrophosphate | HMDB | | 5-Phosphoribosyl pyrophosphate | HMDB | | 5-Phosphoribosyl α-1-pyrophosphate | HMDB | | 5-Phosphorylribose 1-α-diphosphate | HMDB | | Phosphoribosyl pyrophosphate | HMDB | | α-D-5-Phosphoribosyl 1-pyrophosphate | HMDB |
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| Chemical Formula | C5H13O14P3 |
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| Average Molecular Weight | 390.0696 |
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| Monoisotopic Molecular Weight | 389.95181466 |
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| IUPAC Name | [({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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| Traditional Name | phosphoribosylpyrophosphate |
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| CAS Registry Number | 7540-64-9 |
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| SMILES | O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O |
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| 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 |
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| InChI Key | PQGCEDQWHSBAJP-TXICZTDVSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Pentose phosphates |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | - 5-O-phosphono-D-ribofuranosyl diphosphate (CHEBI:17111 )
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| Ontology |
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| Disposition | Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004j-7902000000-513a0a03122b76d768d9 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004i-6952010000-eac4b7259ac1081ff665 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-000i-0009000000-4d49c2b254fa550d7fc4 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-000i-0129000000-1d706d02a4abbeb42ed5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, negative | splash10-004u-0987000000-ea0ae1567abd90f10399 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, negative | splash10-004l-0961000000-703b20987f54fa234a79 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 19V, negative | splash10-004i-1930000000-0b45299b5f0eae24d372 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 24V, negative | splash10-004i-2910000000-9ce95a1b1c6b6ca5768d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 28V, negative | splash10-004i-6900000000-98e568c985ce119eab97 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 32V, negative | splash10-004i-9600000000-4d4d3c26cf4221488cb8 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 38V, negative | splash10-004i-9300000000-ae7ce84c85a837e48257 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 45V, negative | splash10-004i-9100000000-535b36bb64043a2b5e66 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 54V, negative | splash10-004i-9000000000-b83900fdd755592d555a | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0006-0190000000-535b5f43d315fbc182ad | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-004i-9000000000-46d4cee1b5ac630ba9b8 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0a4i-0900000000-8f51c8c38a697fb3a6f0 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-006x-0930000000-6eebf2cc9471f692be90 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-01t9-7900000000-a94c6a883f36818a0855 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-00di-0089000000-73b944f3bcd8c2e5fa58 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-0udi-0079300000-a94093288821d386ab6a | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-0a4i-0001900000-04d2c9666f93d8bb3ec0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-2934000000-e0fcfd13254fd3781439 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dm-6593000000-b295e74d43b0dc625e47 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01r2-7920000000-a021603f22f19c083511 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0509000000-54231bd8f000ab2dd4a0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9301000000-447b996f7510c6ae354b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-54f70df2270a3e4f67d2 | Spectrum |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | |
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 5.72 +/- 0.86 uM | Children (1-13 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 4.9 +/- 2.1 uM | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| Associated Disorders and Diseases |
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| Disease References | None |
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| Associated OMIM IDs | None |
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| External Links |
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| DrugBank ID | DB01632 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB021928 |
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| KNApSAcK ID | C00007296 |
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| Chemspider ID | 7062 |
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| KEGG Compound ID | C00119 |
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| BioCyc ID | PRPP |
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| BiGG ID | 33926 |
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| Wikipedia Link | Phosphoribosyl pyrophosphate |
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| METLIN ID | 5274 |
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| PubChem Compound | 7339 |
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| PDB ID | Not Available |
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| ChEBI ID | 17111 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | PRPP |
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| MarkerDB ID | |
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| References |
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| 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. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes]. Lab Delo. 1977;(12):724-5. [PubMed:75318 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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