Showing Compound Card for 5-Aminoimidazole ribonucleotide (CDB004895)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:47:56 UTC
Updated at2020-11-18 16:38:56 UTC
CannabisDB IDCDB004895
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 A 1-(phosphoribosyl)imidazole that is 5-aminoimidazole in which the proton at position 1 has been replaced by a 5-phospho-beta-D-ribofuranosyl group.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. 5-Aminoimidazole ribonucleotide is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
Chemical FormulaC8H14N3O7P
Average Molecular Weight295.19
Monoisotopic Molecular Weight295.0569
IUPAC Name{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name5-aminoimidazole ribotide
CAS Registry Number25635-88-5
SMILES
NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Trifunctional purine biosynthetic protein adenosine-3GART21q22.11P22102 details
Multifunctional protein ADE2PAICS4q12P22234 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Trifunctional purine biosynthetic protein adenosine-3GART21q22.11P22102 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001235
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022504
KNApSAcK IDC00019655
Chemspider ID141854
KEGG Compound IDC03373
BioCyc ID5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE
BiGG ID41727
Wikipedia Link5-Aminoimidazole_ribotide
METLIN ID6097
PubChem Compound161500
PDB IDNot Available
ChEBI ID138560
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Trifunctional purine biosynthetic protein adenosine-3
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
Enzyme Details
2. Multifunctional protein ADE2
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
P22234
Molecular weight:
47078.82