Showing metabocard for Phosphoribosyl pyrophosphate (BMDB0000280)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
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

Enzyme Details
1. Adenine phosphoribosyltransferase
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
Enzyme Details
2. Hypoxanthine-guanine phosphoribosyltransferase
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
Enzyme Details
3. Ribose-phosphate pyrophosphokinase 1
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
Enzyme Details
4. Nicotinate phosphoribosyltransferase
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
Enzyme Details
5. Nicotinate-nucleotide pyrophosphorylase [carboxylating]
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
Enzyme Details
6. Uridine 5'-monophosphate synthase
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
Enzyme Details
7. Amidophosphoribosyltransferase
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
Enzyme Details
8. Nicotinamide phosphoribosyltransferase
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