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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:39:01 UTC
HMDB IDHMDB0000280
Secondary Accession Numbers
  • HMDB00280
Metabolite Identification
Common NamePhosphoribosyl pyrophosphate
DescriptionPhosphoribosyl 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 through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in adenosine deaminase deficiency. Phosphoribosyl pyrophosphate is a pentosephosphate and it is 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.
Structure
Thumb
Synonyms
Chemical FormulaC5H13O14P3
Average Molecular Weight390.0696
Monoisotopic Molecular Weight389.95181466
IUPAC Name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namephosphoribosylpyrophosphate
CAS Registry Number7540-64-9
SMILES
O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
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 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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue Locations
  • Erythrocyte
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.72 +/- 0.86 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.9 +/- 2.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01632
Phenol Explorer Compound IDNot Available
FooDB IDFDB021928
KNApSAcK IDC00007296
Chemspider ID7062
KEGG Compound IDC00119
BioCyc IDPRPP
BiGG ID33926
Wikipedia LinkPhosphoribosyl pyrophosphate
METLIN ID5274
PubChem Compound7339
PDB IDNot Available
ChEBI ID17111
Food Biomarker OntologyNot Available
VMH IDPRPP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGross, 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.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
Not Available
Gene Name:
PPAT
Uniprot ID:
Q06203
Molecular weight:
57398.52
Reactions
5-Phosphoribosylamine + Pyrophosphate + Glutamic acid → Glutamine + Phosphoribosyl pyrophosphate + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q15274
Molecular weight:
30815.28
Reactions
Nicotinic acid mononucleotide + Pyrophosphate + CO(2) → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
Nicotinic acid mononucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Reactions
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Reactions
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
Xanthylic acid + Pyrophosphate → Xanthine + Phosphoribosyl pyrophosphatedetails
Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
6-Methylmercaptopurine + Phosphoribosyl pyrophosphate → 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphatedetails
Thioguanine + Phosphoribosyl pyrophosphate → 6-Thioguanosine monophosphate + Pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1L1
Uniprot ID:
P21108
Molecular weight:
34838.915
Reactions
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1
Uniprot ID:
P60891
Molecular weight:
12324.195
Reactions
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS2
Uniprot ID:
P11908
Molecular weight:
35054.06
Reactions
Adenosine triphosphate + D-Ribose 5-phosphate → Adenosine monophosphate + Phosphoribosyl pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
UMPS
Uniprot ID:
P11172
Molecular weight:
52221.075
Reactions
Orotidylic acid + Pyrophosphate → Orotic acid + Phosphoribosyl pyrophosphatedetails
Fluorouracil + Phosphoribosyl pyrophosphate → 5-Fluorouridine monophosphate + Pyrophosphatedetails
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to yield nicotinamide mononucleotide, an intermediate in the biosynthesis of NAD. It is the rate limiting component in the mammalian NAD biosynthesis pathway (By similarity).
Gene Name:
NAMPT
Uniprot ID:
P43490
Molecular weight:
55520.8
Reactions
Nicotinamide ribotide + Pyrophosphate → Niacinamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the conversion of nicotinic acid (NA) to NA mononucleotide (NaMN). Essential for NA to increase cellular NAD levels and prevent oxidative stress of the cells.
Gene Name:
NAPRT1
Uniprot ID:
Q6XQN6
Molecular weight:
57577.575
Reactions
Nicotinic acid mononucleotide + Pyrophosphate → Nicotinic acid + Phosphoribosyl pyrophosphatedetails

Only showing the first 10 proteins. There are 11 proteins in total.