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Identification |
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YMDB ID | YMDB00402 |
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Name | Phosphoribosyl pyrophosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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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 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Phosphoribosyl pyrophosphate. |
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Structure | |
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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
- 5-Phospho-α-D-ribose-1-diphosphate
- 5-Phospho-α-D-ribosyl pyrophosphate
- 5-Phosphoribosyl alpha-1-pyrophosphate
- 5-Phosphoribosyl pyrophosphate
- 5-Phosphoribosyl α-1-pyrophosphate
- 5-Phosphorylribose 1-α-diphosphate
- Α-D-5-phosphoribosyl 1-pyrophosphate
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CAS number | 7540-64-9 |
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Weight | Average: 390.0696 Monoisotopic: 389.95181466 |
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InChI Key | PQGCEDQWHSBAJP-TXICZTDVSA-N |
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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)/t2-,3-,4-,5-/m1/s1 |
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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 IUPAC Name | phosphoribosylpyrophosphate |
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Chemical Formula | C5H13O14P3 |
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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] |
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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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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways |
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SMPDB Reactions |
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KEGG Reactions |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | 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 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004i-6952010000-eac4b7259ac1081ff665 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-000i-0009000000-4d49c2b254fa550d7fc4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-000i-0129000000-1d706d02a4abbeb42ed5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, negative | splash10-004u-0987000000-ea0ae1567abd90f10399 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, negative | splash10-004l-0961000000-703b20987f54fa234a79 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 19V, negative | splash10-004i-1930000000-0b45299b5f0eae24d372 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 24V, negative | splash10-004i-2910000000-9ce95a1b1c6b6ca5768d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 28V, negative | splash10-004i-6900000000-98e568c985ce119eab97 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 32V, negative | splash10-004i-9600000000-4d4d3c26cf4221488cb8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 38V, negative | splash10-004i-9300000000-ae7ce84c85a837e48257 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 45V, negative | splash10-004i-9100000000-535b36bb64043a2b5e66 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 54V, negative | splash10-004i-9000000000-b83900fdd755592d555a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0006-0190000000-535b5f43d315fbc182ad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-004i-9000000000-46d4cee1b5ac630ba9b8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0a4i-0900000000-8f51c8c38a697fb3a6f0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-006x-0930000000-6eebf2cc9471f692be90 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-01t9-7900000000-a94c6a883f36818a0855 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-00di-0089000000-73b944f3bcd8c2e5fa58 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-0udi-0079300000-a94093288821d386ab6a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-0a4i-0001900000-04d2c9666f93d8bb3ec0 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-2934000000-e0fcfd13254fd3781439 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dm-6593000000-b295e74d43b0dc625e47 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01r2-7920000000-a021603f22f19c083511 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0509000000-54231bd8f000ab2dd4a0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9301000000-447b996f7510c6ae354b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-54f70df2270a3e4f67d2 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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References |
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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
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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 ( |
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External Links: | |
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