Record Information
Version1.0
Creation Date2016-09-30 22:27:46 UTC
Update Date2020-05-21 16:28:55 UTC
BMDB IDBMDB0000280
Secondary Accession Numbers
  • BMDB00280
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 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Phosphoribosyl pyrophosphate.
Structure
Thumb
Synonyms
ValueSource
5-Phospho-alpha-D-ribose 1-diphosphateChEBI
5-Phosphoribosyl 1-pyrophosphateChEBI
5-Phosphoribosyl diphosphateChEBI
alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)ChEBI
ALPHA-PHOSPHORIBOSYLPYROphosphORIC ACIDChEBI
PhosphoribosylpyrophosphateChEBI
PRib-PPChEBI
PRPPChEBI
5-Phospho-a-D-ribose 1-diphosphateGenerator
5-Phospho-a-D-ribose 1-diphosphoric acidGenerator
5-Phospho-alpha-D-ribose 1-diphosphoric acidGenerator
5-Phospho-α-D-ribose 1-diphosphateGenerator
5-Phospho-α-D-ribose 1-diphosphoric acidGenerator
5-Phosphoribosyl 1-pyrophosphoric acidGenerator
5-Phosphoribosyl diphosphoric acidGenerator
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-PHOSPHORIBOSYLPYROphosphateGenerator
a-PHOSPHORIBOSYLPYROphosphoric acidGenerator
alpha-PHOSPHORIBOSYLPYROphosphateGenerator
Α-phosphoribosylpyrophosphateGenerator
Α-phosphoribosylpyrophosphoric acidGenerator
Phosphoribosylpyrophosphoric acidGenerator
Phosphoribosyl pyrophosphoric acidGenerator
5-Phospho-a-D-ribose-1-diphosphateHMDB
5-Phospho-a-D-ribosyl pyrophosphateHMDB
5-Phospho-alpha-D-ribose-1-diphosphateHMDB
5-Phospho-alpha-D-ribosyl pyrophosphateHMDB
5-Phosphoribose 1-pyrophosphateHMDB
5-Phosphoribosyl 1-diphosphateHMDB
5-Phosphoribosyl a-1-pyrophosphateHMDB
5-Phosphoribosyl-1-pyrophosphateHMDB
5-Phosphorylribose 1-a-diphosphateHMDB
5-Phosphorylribose 1-alpha-diphosphateHMDB
5-Phosphorylribose 1-pyrophosphateHMDB
5-Phosphorylribosyl 1-pyrophosphateHMDB
a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
a-D-5-Phosphoribosyl 1-pyrophosphateHMDB
a-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
alpha-D-5-Phosphoribosyl 1-pyrophosphateHMDB
alpha-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
Phosphoribosyl-1-pyrophosphateHMDB
Phosphoribosyl-pyrophosphateHMDB
PhosphoribosylpyrophosphorateHMDB
PP-Ribose-pHMDB
Pyrophosphate, phosphoribosylHMDB
5-Phospho-α-D-ribose-1-diphosphateHMDB
5-Phospho-α-D-ribosyl pyrophosphateHMDB
5-Phosphoribosyl alpha-1-pyrophosphateHMDB
5-Phosphoribosyl pyrophosphateHMDB
5-Phosphoribosyl α-1-pyrophosphateHMDB
5-Phosphorylribose 1-α-diphosphateHMDB
Α-D-5-phosphoribosyl 1-pyrophosphateHMDB
Phosphoribosyl pyrophosphateHMDB
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability27.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-000i-0009000000-4d49c2b254fa550d7fc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-0129000000-1d706d02a4abbeb42ed5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004u-0987000000-ea0ae1567abd90f10399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004l-0961000000-703b20987f54fa234a79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-1930000000-0b45299b5f0eae24d372View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-2910000000-9ce95a1b1c6b6ca5768dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-6900000000-98e568c985ce119eab97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-004i-9600000000-4d4d3c26cf4221488cb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, negativesplash10-004i-9300000000-ae7ce84c85a837e48257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-004i-9100000000-535b36bb64043a2b5e66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-9000000000-b83900fdd755592d555aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0006-0190000000-535b5f43d315fbc182adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0a4i-0900000000-8f51c8c38a697fb3a6f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-006x-0930000000-6eebf2cc9471f692be90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-01t9-7900000000-a94c6a883f36818a0855View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-00di-0089000000-73b944f3bcd8c2e5fa58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0079300000-a94093288821d386ab6aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-0001900000-04d2c9666f93d8bb3ec0View 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
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Erythrocyte
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000280
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
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 ReferencesNot Available

Enzymes

General function:
Nucleotide transport and metabolism
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:
Q56JW4
Molecular weight:
19537.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
HPRT1
Uniprot ID:
Q3SZ18
Molecular weight:
24498.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
Xanthylic acid + Pyrophosphate → Xanthine + Phosphoribosyl pyrophosphatedetails
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1
Uniprot ID:
Q2HJ58
Molecular weight:
34834.0
Reactions
D-Ribose 5-phosphate + Adenosine triphosphate → Phosphoribosyl pyrophosphate + Adenosine monophosphatedetails
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the first step in the biosynthesis of NAD from nicotinic acid, the ATP-dependent synthesis of beta-nicotinate D-ribonucleotide from nicotinate and 5-phospho-D-ribose 1-phosphate. Helps prevent cellular oxidative stress via its role in NAD biosynthesis.
Gene Name:
NAPRT
Uniprot ID:
A5PK51
Molecular weight:
57871.0
General function:
Coenzyme transport and metabolism
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q3T063
Molecular weight:
31151.0
Reactions
Nicotinic acid mononucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Orotidine 5'-phosphate + diphosphate = orotate + 5-phospho-alpha-D-ribose 1-diphosphate
Gene Name:
UMPS
Uniprot ID:
P31754
Molecular weight:
52229.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
PPAT
Uniprot ID:
F1MV22
Molecular weight:
59900.0
Reactions
5-Phosphoribosylamine + Pyrophosphate + L-Glutamic acid → L-Glutamine + Phosphoribosyl pyrophosphate + Waterdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
NAMPT
Uniprot ID:
F1MJ80
Molecular weight:
53675.0
Reactions
Niacinamide + Phosphoribosyl pyrophosphate → Nicotinamide ribotide + Pyrophosphatedetails