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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:19 UTC
HMDB IDHMDB0001235
Secondary Accession Numbers
  • HMDB0002316
  • HMDB0011609
  • HMDB01235
  • HMDB02316
  • HMDB11609
Metabolite Identification
Common Name5-Aminoimidazole ribonucleotide
Description5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis. It is also the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of pyrimidine biosynthesis. This reaction is mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamine phosphate (TMP), and subsequently to thiamine pyrophosphate (TPP). TPP is an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535 ). 5-Aminoimidazole ribonucleotide is a substrate for a number of proteins including: Scaffold attachment factor B2, Multifunctional protein ADE2, Pulmonary surfactant-associated protein B, Tumor necrosis factor receptor superfamily member 25, Pulmonary surfactant-associated protein C, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B.
Structure
Data?1584118571
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 Weight295.1864
Monoisotopic Molecular Weight295.056936329
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:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available165.6831661259
DarkChem[M-H]-PredictedNot Available158.34531661259
AllCCS[M+H]+PredictedNot Available164.70932859911
AllCCS[M-H]-PredictedNot Available158.23932859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
5-Aminoimidazole ribonucleotide,1TMS,#12580.24https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TMS,#22571.3918https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TMS,#32666.9817https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TMS,#42685.7966https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#12541.949https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#22634.3257https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#32639.0854https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#42628.7244https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#52631.3813https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#62660.984https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#72722.484https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TMS,#82636.986https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TBDMS,#12859.4348https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TBDMS,#22852.7483https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TBDMS,#32920.273https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,1TBDMS,#42942.9275https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#13024.4119https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#23101.4468https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#33111.757https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#43099.1724https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#53112.1772https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#63135.5593https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#73185.891https://arxiv.org/abs/1905.12712
5-Aminoimidazole ribonucleotide,2TBDMS,#83065.6726https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9310000000-83cf50bc3f675ec17ccb2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01vk-9314000000-ed8269ba053b2e3a4fc42017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9130000000-143cf7dfaf8cc77d62802015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-26b4d68163a88586005b2015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-87449f0e16a1690c48732015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-9160000000-50e60dc03e3bb20506362015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9000000000-797c3e0faf96fe4330aa2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e3a71c432cedbcd38922015-09-15View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDAIR
MarkerDB IDNot Available
References
Synthesis ReferenceGroziak 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vetvik H, Grewal HM, Haugen IL, Ahren C, Haneberg B: Mucosal antibodies can be measured in air-dried samples of saliva and feces. J Immunol Methods. 1998 Jun 1;215(1-2):163-72. [PubMed:9744758 ]
  2. Ogata M, Michitsuji H, Fujiki Y: Estimating amounts of toluene inhaled by workers with protective mask using biological indicators of toluene. Toxicol Lett. 1999 Sep 5;108(2-3):233-9. [PubMed:10511267 ]
  3. Chang HK, Weber ME, King M: Mucus transport by high-frequency nonsymmetrical oscillatory airflow. J Appl Physiol (1985). 1988 Sep;65(3):1203-9. [PubMed:3182490 ]
  4. Lawhorn BG, Mehl RA, Begley TP: Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction. Org Biomol Chem. 2004 Sep 7;2(17):2538-46. Epub 2004 Aug 11. [PubMed:15326535 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
Reactions
Adenosine triphosphate + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine → ADP + Phosphate + 5-Aminoimidazole ribonucleotidedetails
Adenosine triphosphate + Phosphoribosylformylglycinamidine → ADP + Phosphate + 5-Aminoimidazole ribonucleotidedetails
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
P22234
Molecular weight:
47078.82
Reactions
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + CO(2)details
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + Carbon dioxidedetails