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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-17 16:54:24 UTC
HMDB IDHMDB0001128
Secondary Accession Numbers
  • HMDB0002347
  • HMDB01128
  • HMDB02347
Metabolite Identification
Common Name5-Phosphoribosylamine
Description5-Phosphoribosylamine, also known as 5-p-beta-D-ribosyl-amine or PRA, 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. The beta-anomer of 5-phospho-D-ribosylamine. 5-Phosphoribosylamine is a very strong basic compound (based on its pKa). 5-Phosphoribosylamine exists in all eukaryotes, ranging from yeast to humans. Within humans, 5-phosphoribosylamine participates in a number of enzymatic reactions. In particular, 5-phosphoribosylamine and L-glutamic acid can be converted into L-glutamine and phosphoribosyl pyrophosphate; which is mediated by the enzyme amidophosphoribosyltransferase. In addition, 5-phosphoribosylamine and glycine can be converted into glycineamideribotide through the action of the enzyme trifunctional purine biosynthetic protein adenosine-3. In humans, 5-phosphoribosylamine is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway.
Structure
Data?1592412864
Synonyms
ValueSource
5-Phospho-beta-D-ribosylamineKEGG
5-Phospho-D-ribosylamineKEGG, ChEBI
5-Phosphoribosyl-1-amineKEGG, ChEBI
5-Phospho-b-D-ribosylamineGenerator
5-Phospho-β-D-ribosylamineGenerator
5-P-beta-D-Ribosyl-amineHMDB
5-Phospho-beta-D-ribosyl-amineHMDB
PRAHMDB
Phosphoribosyl-1-amineHMDB
PhosphoribosylamineHMDB
beta-Phosphoribosyl-1-amineHMDB
β-Phosphoribosyl-1-amineHMDB
Chemical FormulaC5H12NO7P
Average Molecular Weight229.125
Monoisotopic Molecular Weight229.035138255
IUPAC Name{[(2R,3S,4R,5R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name5-phospho-β-D-ribosylamine
CAS Registry Number6062-06-2
SMILES
N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
InChI KeySKCBPEVYGOQGJN-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
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Hemiaminal
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility38.2 g/LALOGPS
logP-2.4ALOGPS
logP-3.5ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area142.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.49 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9200000000-1c4fff9bc3c106e53faaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9741000000-81d2b48c346eaf5bd609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2490000000-890344ea8a2dc31a68cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-8950000000-3968c4c6838390005385Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-696f573fba92b8542f35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9040000000-95218a5e49093dd3dec6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-909c9da9ed8687627fbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d063b8fd7634dcdf6580Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022441
KNApSAcK IDC00007377
Chemspider ID388939
KEGG Compound IDC03090
BioCyc ID5-P-BETA-D-RIBOSYL-AMINE
BiGG ID41182
Wikipedia LinkPhosphoribosylamine
METLIN ID6023
PubChem Compound439905
PDB IDNot Available
ChEBI ID37737
Food Biomarker OntologyNot Available
VMH IDPRAM
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kamal MA, Christopherson RI: Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates. Int J Biochem Cell Biol. 2004 Mar;36(3):545-51. [PubMed:14687931 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
Reactions
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphate + Glycineamideribotidedetails
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphate + Glycineamideribotidedetails
General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
Not Available
Gene Name:
PPAT
Uniprot ID:
Q06203
Molecular weight:
57398.52
Reactions
5-Phosphoribosylamine + Pyrophosphate + L-Glutamic acid → L-Glutamine + Phosphoribosyl pyrophosphate + Waterdetails