Phosphoribosyl pyrophosphate (CHEM034787)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:13:20 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034787
Identification
Common NamePhosphoribosyl pyrophosphate
ClassSmall Molecule
DescriptionA derivative of alpha-D-ribose having a phosphate group at the 5-position and a diphosphate at the 1-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Phospho-alpha-D-ribose 1-diphosphateChEBI
5-Phosphoribosyl 1-pyrophosphateChEBI
5-Phosphoribosyl diphosphateChEBI
alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)ChEBI
ALPHA-PHOSPHORIBOSYLPYROphosphORIC ACIDChEBI
PhosphoribosylpyrophosphateChEBI
PRib-PPChEBI
PRPPChEBI
5-Phospho-a-D-ribose 1-diphosphateGenerator
5-Phospho-a-D-ribose 1-diphosphoric acidGenerator
5-Phospho-alpha-D-ribose 1-diphosphoric acidGenerator
5-Phospho-α-D-ribose 1-diphosphateGenerator
5-Phospho-α-D-ribose 1-diphosphoric acidGenerator
5-Phosphoribosyl 1-pyrophosphoric acidGenerator
5-Phosphoribosyl diphosphoric acidGenerator
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-PHOSPHORIBOSYLPYROphosphateGenerator
a-PHOSPHORIBOSYLPYROphosphoric acidGenerator
alpha-PHOSPHORIBOSYLPYROphosphateGenerator
Α-phosphoribosylpyrophosphateGenerator
Α-phosphoribosylpyrophosphoric acidGenerator
Phosphoribosylpyrophosphoric acidGenerator
Phosphoribosyl pyrophosphoric acidGenerator
5-Phospho-a-D-ribose-1-diphosphateHMDB
5-Phospho-a-D-ribosyl pyrophosphateHMDB
5-Phospho-alpha-D-ribose-1-diphosphateHMDB
5-Phospho-alpha-D-ribosyl pyrophosphateHMDB
5-Phosphoribose 1-pyrophosphateHMDB
5-Phosphoribosyl 1-diphosphateHMDB
5-Phosphoribosyl a-1-pyrophosphateHMDB
5-Phosphoribosyl-1-pyrophosphateHMDB
5-Phosphorylribose 1-a-diphosphateHMDB
5-Phosphorylribose 1-alpha-diphosphateHMDB
5-Phosphorylribose 1-pyrophosphateHMDB
5-Phosphorylribosyl 1-pyrophosphateHMDB
a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
a-D-5-Phosphoribosyl 1-pyrophosphateHMDB
a-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
alpha-D-5-Phosphoribosyl 1-pyrophosphateHMDB
alpha-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
Phosphoribosyl-1-pyrophosphateHMDB
Phosphoribosyl-pyrophosphateHMDB
PhosphoribosylpyrophosphorateHMDB
PP-Ribose-pHMDB
Pyrophosphate, phosphoribosylHMDB
5-Phospho-α-D-ribose-1-diphosphateHMDB
5-Phospho-α-D-ribosyl pyrophosphateHMDB
5-Phosphoribosyl alpha-1-pyrophosphateHMDB
5-Phosphoribosyl pyrophosphateHMDB
5-Phosphoribosyl α-1-pyrophosphateHMDB
5-Phosphorylribose 1-α-diphosphateHMDB
Α-D-5-phosphoribosyl 1-pyrophosphateHMDB
Phosphoribosyl pyrophosphateHMDB
Chemical FormulaC5H13O14P3
Average Molecular Mass390.070 g/mol
Monoisotopic Mass389.952 g/mol
CAS Registry Number7540-64-9
IUPAC Name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namephosphoribosylpyrophosphate
SMILESO[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI IdentifierInChI=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 KeyPQGCEDQWHSBAJP-TXICZTDVSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.6 g/LALOGPS
logP-0.74ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m³·mol⁻¹ChemAxon
Polarizability27.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7902000000-513a0a03122b76d768d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-6952010000-eac4b7259ac1081ff665Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-000i-0009000000-4d49c2b254fa550d7fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-0129000000-1d706d02a4abbeb42ed5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004u-0987000000-ea0ae1567abd90f10399Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004l-0961000000-703b20987f54fa234a79Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-1930000000-0b45299b5f0eae24d372Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-2910000000-9ce95a1b1c6b6ca5768dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-6900000000-98e568c985ce119eab97Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-004i-9600000000-4d4d3c26cf4221488cb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, negativesplash10-004i-9300000000-ae7ce84c85a837e48257Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-004i-9100000000-535b36bb64043a2b5e66Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-9000000000-b83900fdd755592d555aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0006-0190000000-535b5f43d315fbc182adSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0a4i-0900000000-8f51c8c38a697fb3a6f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-006x-0930000000-6eebf2cc9471f692be90Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-01t9-7900000000-a94c6a883f36818a0855Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-00di-0089000000-73b944f3bcd8c2e5fa58Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0079300000-a94093288821d386ab6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-0001900000-04d2c9666f93d8bb3ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-2934000000-e0fcfd13254fd3781439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-6593000000-b295e74d43b0dc625e47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-7920000000-a021603f22f19c083511Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0509000000-54231bd8f000ab2dd4a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9301000000-447b996f7510c6ae354bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-54f70df2270a3e4f67d2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01632
HMDB IDHMDB0000280
FooDB IDFDB021928
Phenol Explorer IDNot Available
KNApSAcK IDC00007296
BiGG ID33926
BioCyc IDPRPP
METLIN ID5274
PDB IDNot Available
Wikipedia LinkPhosphoribosyl pyrophosphate
Chemspider ID7062
ChEBI ID17111
PubChem Compound ID7339
Kegg Compound IDC00119
YMDB IDYMDB00402
ECMDB IDECMDB00280
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22264286
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23509005
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23734909
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes]. Lab Delo. 1977;(12):724-5.
16. Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.