Record Information
Version2.0
Creation Date2012-05-31 10:25:26 -0600
Update Date2015-06-03 15:53:26 -0600
Secondary Accession Numbers
  • ECMDB00280
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
Thumb
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
Weight:Average: 390.0696
Monoisotopic: 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
DescriptionThis compound 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
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability27.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate
Hypoxanthine + Phosphoribosyl pyrophosphate <> Inosinic acid + Pyrophosphate
2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate
Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid
Adenine + Phosphoribosyl pyrophosphate <> Adenosine monophosphate + Pyrophosphate
Adenosine triphosphate + Water + Nicotinic acid + Phosphoribosyl pyrophosphate > ADP + Nicotinamide ribotide + Phosphate + Pyrophosphate
Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Hydrogen ion + Phosphoribosyl pyrophosphate
2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-Phospho-D-ribosyl)anthranilate
Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP
L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate + 5-Phosphoribosylamine
Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate
Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate
Adenosine triphosphate + Ribose 1,5-bisphosphate <> ADP + Phosphoribosyl pyrophosphate
Adenosine monophosphate + Pyrophosphate <> Adenine + Phosphoribosyl pyrophosphate
Uridine 5'-monophosphate + Pyrophosphate <> Uracil + Phosphoribosyl pyrophosphate
Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Phosphoribosyl pyrophosphate
Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate
5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + Water
N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate <> 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate
Inosinic acid + Pyrophosphate <> Hypoxanthine + Phosphoribosyl pyrophosphate
Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate
Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate
Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate
Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate
Nicotinamide ribotide + Pyrophosphate + Carbon dioxide <> Quinolinic acid + Phosphoribosyl pyrophosphate
AICAR + Pyrophosphate <> 5-Amino-4-imidazolecarboxyamide + Phosphoribosyl pyrophosphate
Ribose 1,5-bisphosphate + Adenosine triphosphate <> Phosphoribosyl pyrophosphate + ADP
6-Mercaptopurine + Phosphoribosyl pyrophosphate <> 6-Thioinosine-5'-monophosphate + Pyrophosphate
6-Methylmercaptopurine + Phosphoribosyl pyrophosphate <> 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphate
Thioguanine + Phosphoribosyl pyrophosphate <> 6-Thioguanosine monophosphate + Pyrophosphate
Pyrophosphate + Adenosine monophosphate < Phosphoribosyl pyrophosphate + Adenine
Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate
Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate
Pyrophosphate + Inosinic acid < Phosphoribosyl pyrophosphate + Hypoxanthine
Nicotinamide ribotide + Pyrophosphate < Hydrogen ion + Nicotinic acid + Phosphoribosyl pyrophosphate
Orotidylic acid + Pyrophosphate <> Phosphoribosyl pyrophosphate + Orotic acid
5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + Water
Adenosine triphosphate + D-Ribose-5-phosphate <> Hydrogen ion + Phosphoribosyl pyrophosphate + Adenosine monophosphate
N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate < 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate
Nicotinamide ribotide + Pyrophosphate + Carbon dioxide < Phosphoribosyl pyrophosphate + Quinolinic acid + Hydrogen ion
Ribose 1,5-bisphosphate + Adenosine triphosphate > Phosphoribosyl pyrophosphate + ADP
Pyrophosphate + Uridine 5'-monophosphate < Phosphoribosyl pyrophosphate + Uracil
Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate
Adenosine monophosphate + Pyrophosphate > Adenine + Phosphoribosyl pyrophosphate
Phosphoribosyl-ATP + Pyrophosphate > Adenosine triphosphate + Phosphoribosyl pyrophosphate
Inosinic acid + Pyrophosphate > Hypoxanthine + Phosphoribosyl pyrophosphate
Adenosine triphosphate + D-Ribose-5-phosphate > Adenosine monophosphate + Phosphoribosyl pyrophosphate
Nicotinamide ribotide + Pyrophosphate + Carbon dioxide > Quinolinic acid + Phosphoribosyl pyrophosphate
Adenosine triphosphate + Ribose 1,5-bisphosphate > ADP + Phosphoribosyl pyrophosphate
Nicotinamide ribotide + Pyrophosphate > Nicotinic acid + Phosphoribosyl pyrophosphate
5-Phosphoribosylamine + Pyrophosphate + L-Glutamate > L-Glutamine + Phosphoribosyl pyrophosphate + Water
Orotidylic acid + Pyrophosphate > Orotic acid + Phosphoribosyl pyrophosphate
N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate > 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate
Uridine 5'-monophosphate + Pyrophosphate > Uracil + Phosphoribosyl pyrophosphate
Xanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + Xanthine
Phosphoribosyl pyrophosphate + Hydrogen ion > Pyrophosphate + Phosphoribosyl-ATP + Phosphoribosyl-ATP
2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate
Quinolinic acid + Hydrogen ion + Phosphoribosyl pyrophosphate > Carbon dioxide + Pyrophosphate + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide
Nicotinic acid + Water + Adenosine triphosphate + Phosphoribosyl pyrophosphate > Phosphate + Adenosine diphosphate + Pyrophosphate + nicotinate beta-D-ribonucleotide + ADP + Nicotinamide ribotide
D-Ribose-5-phosphate + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Phosphoribosyl pyrophosphate
Ribose 1,5-bisphosphate + Adenosine triphosphate + Ribose 1,5-bisphosphate > Adenosine diphosphate + Phosphoribosyl pyrophosphate + ADP
Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-Glutamate
Orotic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + Orotidylic acid
Hypoxanthine + Phosphoribosyl pyrophosphate > Inosinic acid + Pyrophosphate
Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphate
Adenine + Phosphoribosyl pyrophosphate > Pyrophosphate + Adenosine monophosphate
Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate
More...

SMPDB Pathways:
NAD biosynthesisPW000829 ThumbThumb?image type=greyscaleThumb?image type=simple
NAD salvagePW000830 ThumbThumb?image type=greyscaleThumb?image type=simple
PRPP BiosynthesisPW000909 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Histidine biosynthesisPW000984 ThumbThumb?image type=greyscaleThumb?image type=simple
Thiamin diphosphate biosynthesisPW002028 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
adenine and adenosine salvage IPW002069 ThumbThumb?image type=greyscaleThumb?image type=simple
adenine and adenosine salvage IIIPW002072 ThumbThumb?image type=greyscaleThumb?image type=simple
guanine and guanosine salvagePW002074 ThumbThumb?image type=greyscaleThumb?image type=simple
histidine biosynthesisPW000810 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
purine ribonucleosides degradationPW002076 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
258± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
153± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
94± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7902000000-513a0a03122b76d768d9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-6952010000-eac4b7259ac1081ff665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-2934000000-e0fcfd13254fd3781439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-6593000000-b295e74d43b0dc625e47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-7920000000-a021603f22f19c083511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0509000000-54231bd8f000ab2dd4a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9301000000-447b996f7510c6ae354bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-54f70df2270a3e4f67d2View 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
External Links:
ResourceLink
CHEBI ID17111
HMDB IDHMDB00280
Pubchem Compound ID7339
Kegg IDC00119
ChemSpider ID7062
WikipediaPhosphoribosyl pyrophosphate
BioCyc IDPRPP
EcoCyc IDPRPP
Ligand ExpoPRP

Enzymes

General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Uniprot ID:
P00904
Molecular weight:
56869
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in magnesium ion binding
Specific function:
ATP + D-ribose 5-phosphate = AMP + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:
prs
Uniprot ID:
P0A717
Molecular weight:
34218
Reactions
ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in orotate phosphoribosyltransferase activity
Specific function:
Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:
pyrE
Uniprot ID:
P0A7E3
Molecular weight:
23567
Reactions
Orotidine 5'-phosphate + diphosphate = orotate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
Gene Name:
upp
Uniprot ID:
P0A8F0
Molecular weight:
22533
Reactions
UMP + diphosphate = uracil + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
This enzyme acts exclusively on hypoxanthine; it does not act on guanine
Gene Name:
hpt
Uniprot ID:
P0A9M2
Molecular weight:
20115
Reactions
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
Acts on guanine, xanthine and to a lesser extent hypoxanthine
Gene Name:
gpt
Uniprot ID:
P0A9M5
Molecular weight:
16971
Reactions
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine.
General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O
Gene Name:
purF
Uniprot ID:
P0AG16
Molecular weight:
56488
Reactions
5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O.
General function:
Involved in protein binding
Specific function:
Belongs to an operon involved in alkylphosphonate uptake and C-P lyase. Exact function not known
Gene Name:
phnN
Uniprot ID:
P16690
Molecular weight:
20729
Reactions
ATP + ribose 1,5-bisphosphate = ADP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate
Gene Name:
pncB
Uniprot ID:
P18133
Molecular weight:
45897
Reactions
Beta-nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA)
Gene Name:
nadC
Uniprot ID:
P30011
Molecular weight:
32762
Reactions
Beta-nicotinate D-ribonucleotide + diphosphate + CO(2) = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in ATP phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of ATP and 5-phosphoribose 1- diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems to be controlled primarily by regulation of hisG enzymatic activity
Gene Name:
hisG
Uniprot ID:
P60757
Molecular weight:
33366
Reactions
1-(5-phospho-D-ribosyl)-ATP + diphosphate = ATP + 5-phospho-alpha-D-ribose 1-diphosphate.
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:
apt
Uniprot ID:
P69503
Molecular weight:
19859
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate.