Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:05:22 UTC |
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Update date | 2024-11-29 22:26:08 UTC |
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Primary ID | FDB021928 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB 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; which is catalyzed by the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A derivative of alpha-D-ribose having a phosphate group at the 5-position and a diphosphate at the 1-position. |
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CAS Number | 7540-64-9 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C5H13O14P3 |
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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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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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Isomeric SMILES | O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O |
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Average Molecular Weight | 390.0696 |
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Monoisotopic Molecular Weight | 389.95181466 |
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Classification |
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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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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Phosphoribosyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004j-7902000000-513a0a03122b76d768d9 | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-6952010000-eac4b7259ac1081ff665 | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Phosphoribosyl pyrophosphate, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-000i-0009000000-4d49c2b254fa550d7fc4 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-000i-0129000000-1d706d02a4abbeb42ed5 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, negative | splash10-004u-0987000000-ea0ae1567abd90f10399 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, negative | splash10-004l-0961000000-703b20987f54fa234a79 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 19V, negative | splash10-004i-1930000000-0b45299b5f0eae24d372 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 24V, negative | splash10-004i-2910000000-9ce95a1b1c6b6ca5768d | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 28V, negative | splash10-004i-6900000000-98e568c985ce119eab97 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 32V, negative | splash10-004i-9600000000-4d4d3c26cf4221488cb8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 38V, negative | splash10-004i-9300000000-ae7ce84c85a837e48257 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 45V, negative | splash10-004i-9100000000-535b36bb64043a2b5e66 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 54V, negative | splash10-004i-9000000000-b83900fdd755592d555a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0006-0190000000-535b5f43d315fbc182ad | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-004i-9000000000-46d4cee1b5ac630ba9b8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-0a4i-0900000000-8f51c8c38a697fb3a6f0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-006x-0930000000-6eebf2cc9471f692be90 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, negative | splash10-01t9-7900000000-a94c6a883f36818a0855 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-00di-0089000000-73b944f3bcd8c2e5fa58 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-0udi-0079300000-a94093288821d386ab6a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-0a4i-0001900000-04d2c9666f93d8bb3ec0 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-2934000000-e0fcfd13254fd3781439 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dm-6593000000-b295e74d43b0dc625e47 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01r2-7920000000-a021603f22f19c083511 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0509000000-54231bd8f000ab2dd4a0 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9301000000-447b996f7510c6ae354b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-54f70df2270a3e4f67d2 | 2015-09-15 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 7062 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00119 |
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Pubchem Compound ID | 7339 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17111 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01632 |
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HMDB ID | HMDB00280 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 33926 |
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KNApSAcK ID | Not Available |
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HET ID | PRP |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Phosphoribosyl pyrophosphate |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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