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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:30:23 UTC
HMDB IDHMDB0001128
Secondary Accession Numbers
  • HMDB01128
  • HMDB02347
Metabolite Identification
Common Name5-Phosphoribosylamine
Description5-phosphoribosylamine, also known as 5-P-beta-D-ribosyl-amine or pra, is a member of the class of compounds known as pentose phosphates. Pentose phosphates are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 5-phosphoribosylamine is soluble (in water) and a moderately acidic compound (based on its pKa). 5-phosphoribosylamine can be found in a number of food items such as purple laver, rowanberry, mamey sapote, and sugar apple, which makes 5-phosphoribosylamine a potential biomarker for the consumption of these food products. 5-phosphoribosylamine exists in all eukaryotes, ranging from yeast to humans. In humans, 5-phosphoribosylamine is involved in several metabolic pathways, some of which include azathioprine pathway, glutamate metabolism, homocarnosinosis, and mercaptopurine pathway. 5-phosphoribosylamine is also involved in several metabolic disorders, some of which include gout or kelley-seegmiller syndrome, xanthinuria type II, xanthine dehydrogenase deficiency (xanthinuria), and aICA-Ribosiduria. Phosphoribosylamine (5PRA) is an intermediate in purine metabolism. It is a precursor to IMP. It is generated from Phosphoribosyl pyrophosphate (PRPP) (Wikipedia). 5-Phosphoribosylamine is a substrate for Amidophosphoribosyltransferase and Trifunctional purine biosynthetic protein adenosine-3..
Structure
Thumb
Synonyms
ValueSource
5-phospho-beta-D-RibosylamineKegg
5-phospho-D-RibosylamineKegg
5-Phosphoribosyl-1-amineKegg
5-phospho-b-D-RibosylamineGenerator
5-phospho-β-D-ribosylamineGenerator
5-P-beta-D-Ribosyl-amineHMDB
5-P-beta-delta-Ribosyl-amineHMDB
5-phospho-beta-D-Ribosyl-amineHMDB
5-phospho-beta-delta-Ribosyl-amineHMDB
5-phospho-beta-delta-RibosylamineHMDB
5-phospho-delta-RibosylamineHMDB
PRAHMDB
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 NumberNot Available
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
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
  • 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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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
Bioavailability1ChemAxon
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, Positivesplash10-002b-9200000000-1c4fff9bc3c106e53faaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9741000000-81d2b48c346eaf5bd609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2490000000-890344ea8a2dc31a68cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-8950000000-3968c4c6838390005385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-696f573fba92b8542f35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9040000000-95218a5e49093dd3dec6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-909c9da9ed8687627fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d063b8fd7634dcdf6580View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
2-Hydroxyglutric Aciduria (D And L Form)Pw000212Pw000212 greyscalePw000212 simpleNot Available
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyPw000070Pw000070 greyscalePw000070 simpleNot Available
AICA-RibosiduriaPw000082Pw000082 greyscalePw000082 simpleNot Available
Adenine phosphoribosyltransferase deficiency (APRT)Pw000511Pw000511 greyscalePw000511 simpleNot Available
Adenosine Deaminase DeficiencyPw000075Pw000075 greyscalePw000075 simpleNot Available
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
FoodDB IDFDB022441
KNApSAcK IDC00007377
Chemspider ID388939
KEGG Compound IDC03090
BioCyc ID5-P-BETA-D-RIBOSYL-AMINE
BiGG ID41182
Wikipedia LinkPhosphoribosylamine
METLIN ID6023
PubChem Compound439905
PDB IDGRF
ChEBI ID37737
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 + Phosphoric acid + Glycineamideribotidedetails
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine → ADP + Phosphoric acid + 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