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Identification
YMDB IDYMDB00317
NamePhosphoribosyl-AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphoribosyl-AMP, also known as 5-phosphoribosyl-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 exists in all living species, ranging from bacteria to humans. Within yeast, phosphoribosyl-AMP participates in a number of enzymatic reactions. In particular, phosphoribosyl-AMP can be biosynthesized from 1-(5-phosphoribosyl)-ATP through its interaction with the enzyme histidine biosynthesis trifunctional protein. In addition, phosphoribosyl-AMP can be converted into phosphoribosylformiminoaicar-phosphate; which is mediated by the enzyme histidine biosynthesis trifunctional protein. In yeast, phosphoribosyl-AMP is involved in the metabolic pathway called histidine biosynthesis pathway.
Structure
Thumb
Synonyms
  • 1-(5-Phosphoribosyl)-AMP
  • 5-phosphoribosyl-AMP
  • N-(5-phospho-D-ribosyl)-AMP
  • N-(5'-phospho-D-ribosyl)-AMP
  • N1-(5-phospho-D-ribosyl)-AMP
CAS numberNot Available
WeightAverage: 559.3157
Monoisotopic: 559.071673493
InChI KeyRTQMRTSPTLIIHM-ZLRMBSEFSA-N
InChIInChI=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)/b16-12+/t5-,6-,8-,9-,10-,11-,14+,15-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-{1-[(2S,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 IUPAC Name[(2R,3S,4R,5R)-5-{1-[(2S,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-iminopurin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
Chemical FormulaC15H23N5O14P2
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N=C([H])N(C2=N[H])[C@@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]
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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.38 g/LALOGPS
logP-2.2ALOGPS
logP-4.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
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
Polarizability47.36 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
SMPDB Reactions
1-(5-phosphoribosyl)-ATP + waterhydron + Pyrophosphate + Phosphoribosyl-AMP
Phosphoribosyl-AMPwater + PhosphoribosylformiminoAICAR-phosphate
water + 1-(5-phosphoribosyl)-ATPPhosphoribosyl-AMP + hydron + Pyrophosphate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mn-9408870000-cc1baeed799987a186dfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dj-9300815000-bc458c0886b752d898dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0429120000-beecfdf73867149bf776JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0925000000-e85297f1f3428f363382JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0934000000-eac6a05d73b6fe7aa32cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-7409080000-3d9f7213b5a73bff11b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9403000000-bb5b8f4886bc364f6d44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8be6c4a98ba2bf3f6c1dJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18374
HMDB IDHMDB12276
Pubchem Compound ID439795
Kegg IDC02741
ChemSpider ID24808237
FOODB IDFDB028908
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBOSYL-AMP

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5- phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Gene Name:
HIS4
Uniprot ID:
P00815
Molecular weight:
87720.5
Reactions
1-(5-phosphoribosyl)-AMP + H(2)O → 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
1-(5-phosphoribosyl)-ATP + H(2)O → 1-(5-phosphoribosyl)-AMP + diphosphate.
L-histidinol + H(2)O + 2 NAD(+) → L-histidine + 2 NADH.