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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. Within yeast, 5-aminoimidazole ribonucleotide participates in a number of enzymatic reactions. In particular, 5-aminoimidazole ribonucleotide can be biosynthesized from 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine; which is mediated by the enzyme phosphoribosylformylglycinamide cyclo-ligase. In addition, 5-aminoimidazole ribonucleotide can be converted into N5-carboxyaminoimidazole ribonucleotide; which is catalyzed by the enzyme N5-carboxyaminoimidazole ribonucleotide synthetase. In yeast, 5-aminoimidazole ribonucleotide is involved in the metabolic pathway called purine nucleotides de novo biosynthesis pathway.
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
Polarizability24.9 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 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
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).