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

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Erythrocyte
Feces
Fibroblasts

Tissue Locations

Erythrocyte
Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192000	Amidophosphoribosyltransferase	Unknown	Q06203	Homo sapiens
MMDBp0192006	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Unknown	Q15274	Homo sapiens
MMDBp0192104	Adenine phosphoribosyltransferase	Enzyme	P07741	Homo sapiens
MMDBp0192133	Hypoxanthine-guanine phosphoribosyltransferase	Unknown	P00492	Homo sapiens
MMDBp0192212	Ribose-phosphate pyrophosphokinase 3	Unknown	P21108	Homo sapiens
MMDBp0192270	Ribose-phosphate pyrophosphokinase 1	Unknown	P60891	Homo sapiens
MMDBp0192274	Ribose-phosphate pyrophosphokinase 2	Unknown	P11908	Homo sapiens
MMDBp0192654	Uridine 5'-monophosphate synthase	Enzyme	P11172	Homo sapiens
MMDBp0195628	Nicotinamide phosphoribosyltransferase	Unknown	P43490	Homo sapiens
MMDBp0195640	Nicotinate phosphoribosyltransferase	Unknown	Q6XQN6	Homo sapiens
MMDBp0196271	Uracil phosphoribosyltransferase homolog	Enzyme	Q96BW1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
NAD+ Signalling Pathway (Cancer)
NAD+ Signalling and Aging

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001763	Niacinamide	Nicotinamide ribotide	Not Available	VMH; KEGG	30371894
MMDBr0001837	Orotidylic acid	Orotic acid	uridine monophosphate synthetase	VMH; KEGG	30371894
MMDBr0002534	Nicotinic acid mononucleotide	Nicotinic acid	Not Available	VMH	17604275
MMDBr0007052	Phosphoribosyl pyrophosphate	1-(5-phosphoribosyl)-ATP	Not Available	VMH	30371894
MMDBr0007263	2-Aminobenzoic acid	N-(5-Phospho-D-ribosyl)anthranilate	Not Available	VMH	30371894
MMDBr0007460	Guanine	Guanosine monophosphate	Not Available	VMH; KEGG	30371894
MMDBr0007508	Phosphoribosyl pyrophosphate	Nicotinic acid mononucleotide	Not Available	VMH; KEGG	30371894
MMDBr0007516	Orotic acid	Orotidylic acid	Not Available	VMH	30371894
MMDBr0007547	D-Ribose-5-phosphate	Phosphoribosyl pyrophosphate	Not Available	VMH	30371894
MMDBr0007600	Xanthylic acid	Phosphoribosyl pyrophosphate	Not Available	VMH	30371894
MMDBr0007646	Nicotinic acid	Nicotinic acid mononucleotide	Not Available	VMH	30371894
MMDBr0007833	L-Glutamine	L-Glutamic acid	Not Available	VMH; KEGG	30371894
MMDBr0007871	Hypoxanthine	Inosinic acid	Not Available	VMH; KEGG	30371894
MMDBr0007993	Phosphoribosyl pyrophosphate	Uridine 5'-monophosphate	Not Available	VMH; KEGG	30371894
MMDBr0010285	Phosphoribosyl pyrophosphate	Uridine 5'-monophosphate	uracil phosphoribosyltransferase homolog	VMH	30371894
MMDBr0010293	Phosphoribosyl pyrophosphate	Xanthylic acid	Not Available	VMH	30371894
MMDBr0010884	Phosphoribosyl pyrophosphate	Xanthylic acid	Not Available	VMH; KEGG	30371894
MMDBr0012674	Nicotinic acid	Nicotinic acid mononucleotide	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	563	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	524	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	184	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	133	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	15	Human feces; Human ; Pig	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	6		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	25	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	19		Metabolic reconstruction
Bacteria	Aquificae	4
Archaea/Archaea	Euryarchaeota	56		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria	Chlamydiae	4	Cat ; Human
Bacteria	Chlorobi	11
Eukaryota/Fungi	Ascomycota	19	Human feces; Human saliva; Human supragingival plaque	Unknown
Eukaryota/Fungi	Basidiomycota	3
Bacteria	Deinococcus-thermus	7
Bacteria	Cyanobacteria	35	Human
Bacteria	nah	1
Bacteria	Thermotogae	10
Bacteria	Chloroflexi	10
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	2
Bacteria	Acidobacteria	3
Bacteria	Gemmatimonadetes	1
Bacteria	Nitrospirae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	4.9	2.1	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	5.72	0.86	uM	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Erythrocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000280

DrugBank ID

DB01632

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Phosphoribosyl pyrophosphate

METLIN ID

5274

PubChem Compound

7339

PDB ID

Not Available

ChEBI ID

17111

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

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:0x0000562ee497c098>

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