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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:11 UTC
Update Date2020-03-10 15:55:13 UTC
HMDB IDHMDB0012276
Secondary Accession Numbers
  • HMDB12276
Metabolite Identification
Common NamePhosphoribosyl-AMP
DescriptionPhosphoribosyl-AMP belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Phosphoribosyl-AMP is a very strong basic compound (based on its pKa). Phosphoribosyl-AMP is a nucleic acid component and is an intermediate in histidine biosynthesis. It is converted from phosphoribosyl-ATP via the enzyme phosphoribosyl-ATP diphosphatase (EC 3.6.1.31). It is then converted to phosphoribosylformiminoAICAR-phosphate via the enzyme phosphoribosyl-AMP cyclohydrolase (EC 3.5.4.19).
Structure
Data?1583855713
Synonyms
ValueSource
1-(5-Phospho-beta-D-ribosyl)-AMPChEBI
1-(5-Phosphoribosyl)-AMPChEBI
5-Phosphoribosyl-AMPChEBI
N1-(5-Phospho-D-ribosyl)-AMPChEBI
Phosphoribosyl-AMPChEBI
1-(5-Phospho-b-D-ribosyl)-AMPGenerator
1-(5-Phospho-β-D-ribosyl)-AMPGenerator
Chemical FormulaC15H23N5O14P2
Average Molecular Weight559.3157
Monoisotopic Molecular Weight559.071673493
IUPAC Name{[(2R,3S,4R,5R)-5-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional NamePhosphoribosyl-AMP
CAS Registry Number1109-75-7
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N
InChI Identifier
InChI=1S/C15H23N5O14P2/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(33-14)1-31-35(25,26)27)20(3-17-7)15-11(24)9(22)6(34-15)2-32-36(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H2,25,26,27)(H2,28,29,30)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
InChI KeyRTQMRTSPTLIIHM-KEOHHSTQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
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 Solubility6.38 g/LALOGPS
logP-2.2ALOGPS
logP-4.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.65ChemAxon
pKa (Strongest Basic)5.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area290.17 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity122.54 m³·mol⁻¹ChemAxon
Polarizability45.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0429120000-498a95153bece6824f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0925000000-814fabe53ab8f719f35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0944000000-4ff1b000ce081e879bbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05bb-6409070000-14dd7aebd9e4f041a818Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9304000000-c370f862b64f5520c773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b35331ba878a60224a03Spectrum
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 IDFDB028908
KNApSAcK IDC00007241
Chemspider ID26333130
KEGG Compound IDC02741
BioCyc IDPHOSPHORIBOSYL-AMP
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11988267
PDB IDNot Available
ChEBI ID18374
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available