Back to Compounds

Showing Compound 5-Aminoimidazole ribonucleotide (FDB022504)

Record Information
Version1.0
Creation date2011-09-21 00:15:02 UTC
Update date2025-11-19 02:41:50 UTC
Primary IDFDB022504
Secondary Accession Numbers
  • FDB030558
Chemical Information
FooDB Name5-Aminoimidazole ribonucleotide
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 humans, 5-aminoimidazole ribonucleotide participates in a number of enzymatic reactions. In particular, 5-aminoimidazole ribonucleotide can be biosynthesized from 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate; which is mediated by the enzyme multifunctional protein ADE2. In addition, 5-aminoimidazole ribonucleotide can be biosynthesized from phosphoribosylformylglycineamidine through its interaction with the enzyme trifunctional purine biosynthetic protein adenosine-3. A 1-(phosphoribosyl)imidazole that is 5-aminoimidazole in which the proton at position 1 has been replaced by a 5-phospho-beta-D-ribofuranosyl group. In humans, 5-aminoimidazole ribonucleotide is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, 5-Aminoimidazole ribonucleotide has been detected, but not quantified in, several different foods, such as cascade huckleberries, anises, red bell peppers, spirulina, and black mulberries. This could make 5-aminoimidazole ribonucleotide a potential biomarker for the consumption of these foods.
CAS Number25635-88-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
1-(5'-Phosphoribosyl)-5-aminoimidazoleChEBI
1-(5-Phospho-D-ribosyl)-5-aminoimidazoleChEBI
5'-Phosphoribosyl-5-aminoimidazoleChEBI
5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazoleChEBI
5-Amino-1-ribofuranosylimidazole 5'-phosphateChEBI
AIRChEBI
Aminoimidazole ribonucleotideChEBI
Aminoimidazole ribotideChEBI
PhosphoribosylaminoimidazoleChEBI
5-Amino-1-(5-phospho-D-ribosyl)imidazoleKegg
5-Amino-1-(5-phospho-beta-D-ribosyl)imidazoleKegg
5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazoleGenerator
5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazoleGenerator
5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazoleGenerator
5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazoleGenerator
5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazoleGenerator
5-Amino-1-ribofuranosylimidazole 5'-phosphoric acidGenerator
5-Amino-1-(5-phospho-b-D-ribosyl)imidazoleGenerator
5-Amino-1-(5-phospho-β-D-ribosyl)imidazoleGenerator
5-Aminoimidazole ribotideHMDB
Aminoimidazole ribotide, (beta-D-ribofuranosyl)-isomerHMDB
Aminoimidazole ribotide, (alpha-D-ribofuranosyl)-isomerHMDB
Aminoimidazole ribotide, phosphonoribofuranosyl-isomerHMDB
1-(5-O-D-Ribosyl)-5-aminoimidazoleKegg
1-(5'-Oribosyl)-5-aminoimidazoleKegg
1-(5'-phosphoribosyl)-5-aminoimidazolehmdb
5-amino-1-(5-O-D-Ribosyl)imidazoleKegg
5-aminoimidazole ribonucleotidehmdb
5-aminoimidazole ribotidehmdb
5'-Oribosyl-5-aminoimidazoleKegg
5'-phosphoribosyl-5-aminoimidazolehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H14N3O7P
IUPAC name{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=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
InChI KeyPDACUKOKVHBVHJ-XVFCMESISA-N
Isomeric SMILESNC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Average Molecular Weight295.1864
Monoisotopic Molecular Weight295.056936329
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Aminoimidazole ribonucleotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9310000000-83cf50bc3f675ec17ccbSpectrum
Predicted GC-MS5-Aminoimidazole ribonucleotide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01vk-9314000000-ed8269ba053b2e3a4fc4Spectrum
Predicted GC-MS5-Aminoimidazole ribonucleotide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9130000000-143cf7dfaf8cc77d62802015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-26b4d68163a88586005b2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-87449f0e16a1690c48732015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-9160000000-50e60dc03e3bb20506362015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9000000000-797c3e0faf96fe4330aa2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e3a71c432cedbcd38922015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2490000000-7dd58fcac26f75e7c46f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-6dd5f8e7028cd1ab65d22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-7542d4d80a10b03631f02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9080000000-e3666a5af349af6427f92021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-2dd173dfe9a30642b89d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7c5243a801196e080ddb2021-09-25View Spectrum
NMRNot Available
ChemSpider ID141854
ChEMBL IDCHEMBL1230914
KEGG Compound IDC03373
Pubchem Compound ID161500
Pubchem Substance IDNot Available
ChEBI ID28843
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01235
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41727
KNApSAcK IDC00019655
HET IDAIR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Trifunctional purine biosynthetic protein adenosine-3GARTP22102
Multifunctional protein ADE2PAICSP22234
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference