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 chemical entities known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • 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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m3·mol-1ChemAxon
Polarizability27.45 Å3ChemAxon
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 Pw000829Pw000829 greyscalePw000829 simple
NAD salvagePW000830 Pw000830Pw000830 greyscalePw000830 simple
PRPP BiosynthesisPW000909 Pw000909Pw000909 greyscalePw000909 simple
Pyrimidine metabolismPW000942 Pw000942Pw000942 greyscalePw000942 simple
Secondary Metabolites: Histidine biosynthesisPW000984 Pw000984Pw000984 greyscalePw000984 simple
Thiamin diphosphate biosynthesisPW002028 Pw002028Pw002028 greyscalePw002028 simple
Tryptophan metabolismPW000815 Pw000815Pw000815 greyscalePw000815 simple
adenine and adenosine salvage IPW002069 Pw002069Pw002069 greyscalePw002069 simple
adenine and adenosine salvage IIIPW002072 Pw002072Pw002072 greyscalePw002072 simple
guanine and guanosine salvagePW002074 Pw002074Pw002074 greyscalePw002074 simple
histidine biosynthesisPW000810 Pw000810Pw000810 greyscalePw000810 simple
purine nucleotides de novo biosynthesisPW000910 Pw000910Pw000910 greyscalePw000910 simple
purine nucleotides de novo biosynthesis 1435709748PW000960 Pw000960Pw000960 greyscalePw000960 simple
purine nucleotides de novo biosynthesis 2PW002033 Pw002033Pw002033 greyscalePw002033 simple
purine ribonucleosides degradationPW002076 Pw002076Pw002076 greyscalePw002076 simple
tryptophan metabolism IIPW001916 Pw001916Pw001916 greyscalePw001916 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
GC-MSGC-MS Spectrum - GC-MSsplash10-004j-7902000000-513a0a03122b76d768d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-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.