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Identification
YMDB IDYMDB00065
Name5-Aminoimidazole ribonucleotide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Aminoimidazole ribonucleotide, also known as 5'-phosphoribosyl-5-aminoimidazole or AIR, 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-Aminoimidazole ribonucleotide is a very strong basic compound (based on its pKa). 5-Aminoimidazole ribonucleotide exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 1-(5-Phospho-D-ribosyl)-5-aminoimidazole
  • 1-(5'-phosphoribosyl)-5-aminoimidazole
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole
  • 5-aminoimidazole ribonucleotide
  • 5-aminoimidazole ribotide
  • 5'-phosphoribosyl-5-aminoimidazole
  • AIR
  • Aminoimidazole ribotide
  • 5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole
  • 5-Amino-1-ribofuranosylimidazole 5'-phosphate
  • Aminoimidazole ribonucleotide
  • Phosphoribosylaminoimidazole
  • 5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole
  • 5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole
  • 5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole
  • 5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole
  • 5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole
  • 5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole
  • 5-Amino-1-ribofuranosylimidazole 5'-phosphoric acid
  • 5-Amino-1-(5-phospho-b-D-ribosyl)imidazole
  • 5-Amino-1-(5-phospho-β-D-ribosyl)imidazole
  • Aminoimidazole ribotide, (beta-D-ribofuranosyl)-isomer
  • Aminoimidazole ribotide, (alpha-D-ribofuranosyl)-isomer
  • Aminoimidazole ribotide, phosphonoribofuranosyl-isomer
CAS number25635-88-5
WeightAverage: 295.1864
Monoisotopic: 295.056936329
InChI KeyPDACUKOKVHBVHJ-XVFCMESISA-N
InChIInChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name5-aminoimidazole ribotide
Chemical FormulaC8H14N3O7P
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=NC([H])=C1N([H])[H])C([H])([H])OP(=O)(O[H])O[H]
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
  • Imidazole ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Aminoimidazole
  • Alkyl phosphate
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Primary amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.38 g/LALOGPS
logP-2.3ALOGPS
logP-4.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)7.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.44 m³·mol⁻¹ChemAxon
Polarizability24.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
Thiamine metabolismec00730 Map00730
SMPDB Reactions
2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + Adenosine triphosphate5-Aminoimidazole ribonucleotide + phosphate + ADP + hydron
5-Aminoimidazole ribonucleotide + Hydrogen carbonate + Adenosine triphosphateN5-Carboxyaminoimidazole ribonucleotide + ADP + phosphate + hydron
KEGG Reactions
5-Aminoimidazole ribonucleotide + hydronGlycolaldehyde + phosphate + 4-amino-5-hydroxymethyl-2-methylpyrimidine
5-Aminoimidazole ribonucleotide + Carbon dioxide5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + hydron
Adenosine triphosphate + 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine5-Aminoimidazole ribonucleotide + phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9310000000-83cf50bc3f675ec17ccbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01vk-9314000000-ed8269ba053b2e3a4fc4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9130000000-143cf7dfaf8cc77d6280JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-26b4d68163a88586005bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-87449f0e16a1690c4873JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-9160000000-50e60dc03e3bb2050636JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9000000000-797c3e0faf96fe4330aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e3a71c432cedbcd3892JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2490000000-7dd58fcac26f75e7c46fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-6dd5f8e7028cd1ab65d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-7542d4d80a10b03631f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9080000000-e3666a5af349af6427f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-2dd173dfe9a30642b89dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7c5243a801196e080ddbJSpectraViewer
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
1D NMR13C 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:Groziak M P; Bhat B; Leonard N J Nonenzymatic synthesis of 5-aminoimidazole ribonucleoside and recognition of its facile rearrangement. Proceedings of the National Academy of Sciences of the United States of America (1988), 85(19), 7174-6.
External Links:
ResourceLink
CHEBI ID28843
HMDB IDHMDB01235
Pubchem Compound ID161500
Kegg IDC03373
ChemSpider ID141854
FOODB IDFDB022504
Wikipedia5-amino-1-(5-phospho-D-ribosyl)imidazole
BioCyc ID5-PHOSPHORIBOSYL-5-AMINOIMIDAZOL

Enzymes

General function:
Involved in catalytic activity
Specific function:
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide
Gene Name:
ADE5
Uniprot ID:
P07244
Molecular weight:
86067.39844
Reactions
ATP + 5-phospho-D-ribosylamine + glycine → ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide.
ATP + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine → ADP + phosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole.
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxylate = 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2)
Gene Name:
ADE2
Uniprot ID:
P21264
Molecular weight:
62338.69922
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2).