MiMeDB: Showing metabocard for Phosphoribosyl pyrophosphate (MMDBc0029489)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:22 UTC

Update Date

2024-10-13 09:47:00 UTC

Metabolite ID

MMDBc0029489

Metabolite Identification

Common 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

Synonyms

Value	Source
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
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
Phosphoribosyl pyrophosphoric 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	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
Α-D-5-phosphoribosyl 1-pyrophosphate	HMDB
Phosphoribosyl pyrophosphate	HMDB

Molecular Formula

C₅H₁₃O₁₄P₃

Average Mass

390.0696

Monoisotopic Mass

389.95181466

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

7540-64-9

SMILES

Not Available

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

InChI Key

PQGCEDQWHSBAJP-TXICZTDVSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

General References

Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes]. Lab Delo. 1977;(12):724-5. [PubMed:75318 ]
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. doi: 10.1136/ard.36.3.261. [PubMed:141914 ]
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. doi: 10.1159/000175597. [PubMed:172821 ]
Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6. doi: 10.1007/978-1-4613-4223-6_34. [PubMed:193371 ]
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 ]
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. doi: 10.1016/0009-8981(77)90308-4. [PubMed:195752 ]
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. doi: 10.1111/j.1445-5994.1975.tb03054.x. [PubMed:1061547 ]
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. doi: 10.1016/0009-8981(91)90286-l. [PubMed:1663846 ]
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. doi: 10.1007/BF01799493. [PubMed:2437388 ]
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. doi: 10.1016/0003-2697(87)90056-x. [PubMed:2437821 ]
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. doi: 10.3181/00379727-186-42590. [PubMed:2442765 ]
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 ]
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. doi: 10.1007/BF01799869. [PubMed:2459496 ]
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. doi: 10.1016/0167-4838(89)90065-4. [PubMed:2535789 ]
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 ]
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 ]
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 ]
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. doi: 10.1042/cs0670249. [PubMed:6744792 ]
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. doi: 10.1016/s0925-4439(99)00103-9. [PubMed:10657589 ]
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. doi: 10.1074/jbc.M011103200. Epub 2001 Apr 4. [PubMed:11290738 ]

Showing metabocard for Phosphoribosyl pyrophosphate (MMDBc0029489)

MOL for #<Metabolite:0x0000562307698f68>

3D MOL for #<Metabolite:0x0000562307698f68>

3D SDF for #<Metabolite:0x0000562307698f68>

3D-SDF for #<Metabolite:0x0000562307698f68>

PDB for #<Metabolite:0x0000562307698f68>

3D PDB for #<Metabolite:0x0000562307698f68>

SMILES for #<Metabolite:0x0000562307698f68>

INCHI for #<Metabolite:0x0000562307698f68>

Structure for #<Metabolite:0x0000562307698f68>

3D Structure for #<Metabolite:0x0000562307698f68>