Record Information
Version2.0
Creation Date2012-05-31 13:48:06 -0600
Update Date2015-06-03 15:53:52 -0600
Secondary Accession Numbers
  • ECMDB01235
Identification
Name:5-Aminoimidazole ribonucleotide
Description5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis, the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of the pyrimidine biosynthesis in a reaction mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamin phosphate (TMP), and subsequently to thiamin pyrophosphate (TPP), an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535) 5-Aminoimidazole ribonucleotide is a substrate for Scaffold attachment factor B2, Multifunctional protein ADE2, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B.
Structure
Thumb
Synonyms:
  • 1-(5'-Phosphoribosyl)-5-aminoimidazole
  • 1-(5-Phospho-D-ribosyl)-5-aminoimidazole
  • 5'-Phosphoribosyl-5-aminoimidazole
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole
  • 5-Amino-1-(5-phospho-β-D-ribosyl)imidazole
  • 5-Aminoimidazole ribonucleotide
  • 5-Aminoimidazole ribotide
  • AIR
  • Aminoimidazole ribotide
  • Phosphoribosylaminoimidazole
Chemical Formula:C8H14N3O7P
Weight:Average: 295.1864
Monoisotopic: 295.056936329
InChI Key:PDACUKOKVHBVHJ-XVFCMESISA-N
InChI: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
CAS number:25635-88-5
IUPAC Name:{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:5-aminoimidazole ribotide
SMILES:NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
5-Aminoimidazole ribonucleotide + Adenosine triphosphate + Hydrogen carbonate > 5-Phosphoribosyl-5-carboxyaminoimidazole + ADP + Hydrogen ion + Phosphate
Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate
5-Aminoimidazole ribonucleotide + Water + NAD > 4-Amino-2-methyl-5-phosphomethylpyrimidine +2 Formic acid +3 Hydrogen ion + NADH
4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + Phosphate + 5-Aminoimidazole ribonucleotide
Adenosine triphosphate + 5-Aminoimidazole ribonucleotide + Hydrogen carbonate <> ADP + Phosphate + 5-Carboxyamino-1-(5-phospho-D-ribosyl)imidazole + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole
Adenosine triphosphate + Phosphoribosylformylglycineamidine > Hydrogen ion + ADP + Phosphate + 5-Aminoimidazole ribonucleotide
5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion
5-Aminoimidazole ribonucleotide + Adenosine triphosphate + Hydrogen carbonate > Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP + Phosphate
Adenosine triphosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine > ADP + Inorganic phosphate + 5-Aminoimidazole ribonucleotide
Adenosine triphosphate + 5-Aminoimidazole ribonucleotide + Carbonic acid > ADP + Inorganic phosphate + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole
5-Aminoimidazole ribonucleotide + S-adenosyl-L-methionine > 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Aminoimidazole ribonucleotide + Carbon dioxide
2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + Adenosine triphosphate > 5-Aminoimidazole ribonucleotide + Phosphate + Adenosine diphosphate + Hydrogen ion + ADP
5-Aminoimidazole ribonucleotide + Hydrogen carbonate + Adenosine triphosphate > N5-Carboxyaminoimidazole ribonucleotide + Adenosine diphosphate + Phosphate +2 Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP
5-Aminoimidazole ribonucleotide + S-adenosyl-L-methionine >3 Hydrogen ion + CO + Formic acid + L-Methionine + 5'-Deoxyadenosine + 4-amino-2-methyl-5-phosphomethylpyrimidine
Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP +5 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate
4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
Adenosine triphosphate + 5 5-Aminoimidazole ribonucleotide + Hydrogen carbonate <> ADP + Phosphate +5 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole
4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
SMPDB Pathways:
Thiamin diphosphate biosynthesisPW002028 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis PWY-6890
  • 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121
  • 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122
  • inosine-5'-phosphate biosynthesis I PWY-6123
  • superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9310000000-83cf50bc3f675ec17ccbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01vk-9314000000-ed8269ba053b2e3a4fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9130000000-143cf7dfaf8cc77d6280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-26b4d68163a88586005bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-87449f0e16a1690c4873View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-9160000000-50e60dc03e3bb2050636View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9000000000-797c3e0faf96fe4330aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9e3a71c432cedbcd3892View in MoNA
References
References:
  • Chang HK, Weber ME, King M: Mucus transport by high-frequency nonsymmetrical oscillatory airflow. J Appl Physiol. 1988 Sep;65(3):1203-9. Pubmed: 3182490
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lawhorn, B. G., Mehl, R. A., Begley, T. P. (2004). "Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction." Org Biomol Chem 2:2538-2546. Pubmed: 15326535
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
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.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28843
HMDB IDHMDB01235
Pubchem Compound ID161500
Kegg IDC03373
ChemSpider ID141854
Wikipedia ID5-Aminoimidazole_ribotide
BioCyc ID5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE
EcoCyc ID5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE
Ligand ExpoAIR

Enzymes

General function:
Involved in catalytic activity
Specific function:
ATP + 2-(formamido)-N(1)-(5-phospho-D- ribosyl)acetamidine = ADP + phosphate + 5-amino-1-(5-phospho-D- ribosyl)imidazole
Gene Name:
purM
Uniprot ID:
P08178
Molecular weight:
36854
Reactions
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:
Possesses an ATPase activity that is dependent on the presence of AIR (aminoimidazole ribonucleotide). The association of purK and purE produces an enzyme complex capable of converting AIR to CAIR efficiently under physiological condition
Gene Name:
purK
Uniprot ID:
P09029
Molecular weight:
39461
Reactions
ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole + HCO(3)(-) = ADP + phosphate + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole.
General function:
Involved in thiamine biosynthetic process
Specific function:
Catalyzes the synthesis of the hydroxymethylpyrimidine phosphate (HMP-P) moiety of thiamine from aminoimidazole ribotide (AIR) in a radical S-adenosyl-L-methionine (SAM)-dependent reaction
Gene Name:
thiC
Uniprot ID:
P30136
Molecular weight:
70850
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole + S-adenosyl-L-methionine = 4-amino-2-methyl-5-phosphomethylpyrimidine + 5'-deoxyadenosine + L-methionine + formate + CO.