P. aeruginosa Metabolome Database: Phosphoribosyl pyrophosphate (PAMDB000115)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000115

Identification

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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-D-5-P-RibosylPP
α-D-5-phosphoribosylPP
5-phospho-a-D-Ribose 1-diphosphate
5-phospho-a-D-Ribose 1-diphosphoric acid
5-Phospho-a-D-ribose-1-diphosphate
5-phospho-a-D-Ribose-1-diphosphoric acid
5-Phospho-a-D-ribosyl pyrophosphate
5-phospho-a-D-Ribosyl pyrophosphoric acid
5-phospho-a-D-Riobse 1-diphosphate
5-phospho-a-D-Riobse 1-diphosphoric acid
5-phospho-a-delta-Ribose 1-diphosphate
5-phospho-a-delta-Ribose 1-diphosphoric acid
5-phospho-a-delta-Ribose-1-diphosphate
5-phospho-a-delta-Ribose-1-diphosphoric acid
5-phospho-a-delta-Ribosyl pyrophosphate
5-phospho-a-delta-Ribosyl pyrophosphoric acid
5-phospho-a-δ-Ribose 1-diphosphate
5-phospho-a-δ-Ribose 1-diphosphoric acid
5-phospho-a-δ-Ribose-1-diphosphate
5-phospho-a-δ-Ribose-1-diphosphoric acid
5-phospho-a-δ-Ribosyl pyrophosphate
5-phospho-a-δ-Ribosyl pyrophosphoric acid
5-Phospho-alpha-D-ribose 1-diphosphate
5-phospho-alpha-D-Ribose 1-diphosphoric acid
5-Phospho-alpha-D-ribose-1-diphosphate
5-phospho-alpha-D-Ribose-1-diphosphoric acid
5-Phospho-alpha-D-ribosyl pyrophosphate
5-phospho-alpha-D-Ribosyl pyrophosphoric acid
5-Phospho-alpha-D-riobse 1-diphosphate
5-phospho-alpha-D-Riobse 1-diphosphoric acid
5-Phospho-alpha-delta-ribose 1-diphosphate
5-phospho-alpha-delta-Ribose 1-diphosphoric acid
5-Phospho-alpha-delta-ribose-1-diphosphate
5-phospho-alpha-delta-Ribose-1-diphosphoric acid
5-Phospho-alpha-delta-ribosyl pyrophosphate
5-phospho-alpha-delta-Ribosyl pyrophosphoric acid
5-Phospho-ribosyl-pyrophosphate
5-phospho-Ribosyl-pyrophosphoric acid
5-phospho-α-D-Ribose 1-diphosphate
5-phospho-α-D-Ribose 1-diphosphoric acid
5-phospho-α-D-Ribose-1-diphosphate
5-phospho-α-D-Ribose-1-diphosphoric acid
5-phospho-α-D-Ribosyl pyrophosphate
5-phospho-α-D-Ribosyl pyrophosphoric acid
5-phospho-α-D-Riobse 1-diphosphate
5-phospho-α-D-Riobse 1-diphosphoric acid
5-phospho-α-δ-Ribose 1-diphosphate
5-phospho-α-δ-Ribose 1-diphosphoric acid
5-phospho-α-δ-Ribose-1-diphosphate
5-phospho-α-δ-Ribose-1-diphosphoric acid
5-phospho-α-δ-Ribosyl pyrophosphate
5-phospho-α-δ-Ribosyl pyrophosphoric acid
5-Phosphoribose 1-pyrophosphate
5-Phosphoribose 1-pyrophosphoric acid
5-Phosphoribosyl 1-diphosphate
5-Phosphoribosyl 1-diphosphoric acid
5-Phosphoribosyl 1-pyrophosphate
5-Phosphoribosyl 1-pyrophosphoric acid
5-Phosphoribosyl a-1-pyrophosphate
5-Phosphoribosyl a-1-pyrophosphoric acid
5-Phosphoribosyl diphosphate
5-Phosphoribosyl diphosphoric acid
5-Phosphoribosyl-1-PP
5-Phosphoribosyl-1-pyrophosphate
5-Phosphoribosyl-1-pyrophosphoric acid
5-Phosphoribosyl-PP
5-Phosphoribosylpyrophosphate
5-Phosphoribosylpyrophosphoric acid
5-Phosphorylribose 1-a-diphosphate
5-Phosphorylribose 1-a-diphosphoric acid
5-Phosphorylribose 1-alpha-diphosphate
5-Phosphorylribose 1-alpha-diphosphoric acid
5-Phosphorylribose 1-pyrophosphate
5-Phosphorylribose 1-pyrophosphoric acid
5-Phosphorylribose 1-α-diphosphate
5-Phosphorylribose 1-α-diphosphoric acid
5-Phosphorylribosyl 1-pyrophosphate
5-Phosphorylribosyl 1-pyrophosphoric acid
A-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
a-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-D-5-P-RibosylPP
A-D-5-Phosphoribosyl 1-pyrophosphate
a-D-5-Phosphoribosyl 1-pyrophosphoric acid
a-D-5-PhosphoribosylPP
A-D-Ribofuranose 5-phosphate 1-pyrophosphate
a-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
A-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
a-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
a-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
a-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-delta-5-Phosphoribosyl 1-pyrophosphate
a-delta-5-Phosphoribosyl 1-pyrophosphoric acid
a-delta-Ribofuranose 5-phosphate 1-pyrophosphate
a-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
a-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
a-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-δ-5-Phosphoribosyl 1-pyrophosphate
a-δ-5-Phosphoribosyl 1-pyrophosphoric acid
a-δ-Ribofuranose 5-phosphate 1-pyrophosphate
a-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
alpha-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
Alpha-D-5-P-RibosylPP
Alpha-D-5-Phosphoribosyl 1-pyrophosphate
alpha-D-5-Phosphoribosyl 1-pyrophosphoric acid
Alpha-D-5-PhosphoribosylPP
Alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate
alpha-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
alpha-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
Alpha-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
alpha-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
Alpha-delta-5-Phosphoribosyl 1-pyrophosphate
alpha-delta-5-Phosphoribosyl 1-pyrophosphoric acid
Alpha-delta-Ribofuranose 5-phosphate 1-pyrophosphate
alpha-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Phosphoribosyl pyrophosphate
Phosphoribosyl pyrophosphoric acid
Phosphoribosyl-1-pyrophosphate
Phosphoribosyl-1-pyrophosphoric acid
Phosphoribosyl-pyrophosphate
Phosphoribosyl-pyrophosphoric acid
Phosphoribosylpyrophosphate
Phosphoribosylpyrophosphorate
Phosphoribosylpyrophosphoric acid
PP-Ribose-P
PRib-PP
PRPP
α-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
α-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
α-D-5-P-RibosylPP
α-D-5-Phosphoribosyl 1-pyrophosphate
α-D-5-Phosphoribosyl 1-pyrophosphoric acid
α-D-5-PhosphoribosylPP
α-D-Ribofuranose 5-phosphate 1-pyrophosphate
α-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
α-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
α-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
α-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
α-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
α-δ-5-Phosphoribosyl 1-pyrophosphate
α-δ-5-Phosphoribosyl 1-pyrophosphoric acid
α-δ-Ribofuranose 5-phosphate 1-pyrophosphate
α-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid

Chemical Formula:

C₅H₁₃O₁₄P₃

Average Molecular Weight:

390.0696

Monoisotopic Molecular Weight:

389.95181466

InChI Key:

PQGCEDQWHSBAJP-TXICZTDVSA-N

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

CAS number:

7540-64-9

IUPAC Name:

[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional IUPAC Name:

phosphoribosylpyrophosphate

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Oxolane
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

5-O-phosphono-D-ribofuranosyl diphosphate (CHEBI:17111 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	11.6 mg/mL	ALOGPS
logP	-0.74	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	62.58 m³·mol^-1	ChemAxon
Polarizability	27.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

More...

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Drug metabolism - other enzymes pae00983
Histidine metabolism pae00340
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Nicotinate and nicotinamide metabolism pae00760
Pentose phosphate pathway pae00030
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Purine metabolism pae00230
Pyrimidine metabolism pae00240
Tryptophan metabolism pae00380

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-2934000000-e0fcfd13254fd3781439	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-6593000000-b295e74d43b0dc625e47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01r2-7920000000-a021603f22f19c083511	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0509000000-54231bd8f000ab2dd4a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9301000000-447b996f7510c6ae354b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-54f70df2270a3e4f67d2	View in MoNA

References

References:

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
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
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
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
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
Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes] Lab Delo. 1977;(12):724-5. Pubmed: 75318
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
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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
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
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
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
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
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
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
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
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
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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
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
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

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 (

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17111
HMDB ID	HMDB00280
Pubchem Compound ID	7339
Kegg ID	C00119
ChemSpider ID	7062
Wikipedia	Phosphoribosyl pyrophosphate
BioCyc ID	PRPP
EcoCyc ID	PRPP
Ligand Expo	PRP

Phosphoribosyl pyrophosphate (PAMDB000115)

Structure for Phosphoribosyl pyrophosphate (PAMDB000115)