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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:18:55 UTC
HMDB IDHMDB0001128
Secondary Accession Numbers
  • HMDB0002347
  • HMDB01128
  • HMDB02347
Metabolite Identification
Common Name5-Phosphoribosylamine
Description5-Phosphoribosylamine 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. 5-Phosphoribosylamine exists in all eukaryotes, ranging from yeast to plants to humans. In humans, 5-phosphoribosylamine is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. 5-Phosphoribosylamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 5-phosphoribosylamine a potential biomarker for the consumption of these foods. 5-Phosphoribosylamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 5-Phosphoribosylamine.
Structure
Data?1592412864
Synonyms
ValueSource
5-Phospho-D-ribosylamineChEBI
5-Phosphoribosyl-1-amineChEBI
5-Phospho-beta-D-ribosylamineKegg
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
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility38.2 g/LALOGPS
logP10(-2.4) g/LALOGPS
logP10(-3.5) g/LChemAxon
logS10(-0.78) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.55931661259
DarkChem[M+H]+150.55931661259
DarkChem[M-H]-146.65731661259
DarkChem[M-H]-146.65731661259
AllCCS[M+H]+150.0232859911
AllCCS[M-H]-140.5732859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Phosphoribosylamine,1TMS,#1C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N)[C@@H]1O2107.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TMS,#2C[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O)[C@H]1O2109.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TMS,#3C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N)[C@H](O)[C@@H]1O2097.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TMS,#4C[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O2164.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#1C[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O)[C@H]1O[Si](C)(C)C2099.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#2C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N)[C@@H]1O2145.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#3C[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]1O2129.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#4C[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@H]1O2137.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#5C[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O[Si](C)(C)C2135.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#6C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N)[C@H](O)[C@@H]1O)O[Si](C)(C)C2116.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#7C[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]1O2205.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TMS,#8C[Si](C)(C)N([C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O)[Si](C)(C)C2204.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N)[C@@H]1O2352.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O)[C@H]1O2366.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TBDMS,#3CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N)[C@H](O)[C@@H]1O2352.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,1TBDMS,#4CC(C)(C)[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O2390.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O)[C@H]1O[Si](C)(C)C(C)(C)C2533.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N)[C@@H]1O2589.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#3CC(C)(C)[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2561.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](N)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@H]1O2596.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#5CC(C)(C)[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2562.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#6CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C2570.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#7CC(C)(C)[Si](C)(C)N[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O2650.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5-Phosphoribosylamine,2TBDMS,#8CC(C)(C)[Si](C)(C)N([C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O)[Si](C)(C)C(C)(C)C2629.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phosphoribosylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9200000000-1c4fff9bc3c106e53faa2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phosphoribosylamine GC-MS (2 TMS) - 70eV, Positivesplash10-03dj-9741000000-81d2b48c346eaf5bd6092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phosphoribosylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phosphoribosylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 10V, Positive-QTOFsplash10-001i-2490000000-890344ea8a2dc31a68cd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 20V, Positive-QTOFsplash10-01q9-8950000000-3968c4c68383900053852016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 40V, Positive-QTOFsplash10-0007-9100000000-696f573fba92b8542f352016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 10V, Negative-QTOFsplash10-004i-9040000000-95218a5e49093dd3dec62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 20V, Negative-QTOFsplash10-004i-9000000000-909c9da9ed8687627fbe2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 40V, Negative-QTOFsplash10-004i-9000000000-d063b8fd7634dcdf65802016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 10V, Positive-QTOFsplash10-03e9-0900000000-a28a2870d14f9b514efa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 20V, Positive-QTOFsplash10-03yi-2900000000-3f959957fd3503d8f28b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 40V, Positive-QTOFsplash10-052b-9000000000-69bd1484fc7665f256af2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 10V, Negative-QTOFsplash10-004i-8090000000-2ebfcb2a817d0e5198a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phosphoribosylamine 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
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