N5-Carboxyaminoimidazole ribonucleotide (ECMDB01317) (M2MDB000337)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-05-31 13:49:51 -0600
Update Date2015-09-17 15:41:48 -0600
Secondary Accession Numbers
  • ECMDB01317
Identification
Name:N5-Carboxyaminoimidazole ribonucleotide
DescriptionN5-carboxyaminoimidazole ribonucleotide is a member of the chemical class known as 1-Phosphoribosyl-imidazoles. These are organic compounds containing the imidazole ring linked to a ribose phosphate through a 1-2 bond. The carbamic acid, N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) is an intermediate in purine biosynthesis in E. coli. (PMID 7918411) Formation of 4-carboxy-5-aminoimidazole ribonucleotide (CAIR) in the purine pathway in most prokaryotes requires ATP, HCO3-, aminoimidazole ribonucleotide (AIR), and the gene products PurK and PurE. PurK catalyzes the conversion of AIR to N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) in a reaction that requires both ATP and HCO3-. PurE catalyzes the unusual rearrangement of N5-CAIR to CAIR.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 5-Aminoimidazol-4-carboxamide ribonucleotide
  • 5-Phosphoribosyl-5-carboxyaminoimidazole
  • N5-CAIR
  • N5-CAIR
  • N5-carboxyaminoimidazole ribonucleotide
Chemical Formula:C9H14N3O9P
Weight:Average: 339.1959
Monoisotopic: 339.046765573
InChI Key:JHLXDWGVSYMXPL-UHFFFAOYSA-N
InChI:InChI=1S/C9H14N3O9P/c13-6-4(2-20-22(17,18)19)21-8(7(6)14)12-3-10-1-5(12)11-9(15)16/h1,3-4,6-8,11,13-14H,2H2,(H,15,16)(H2,17,18,19)
CAS number:Not Available
IUPAC Name:5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboxylate
Traditional IUPAC Name:5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazole-4-carboxylate
SMILES:OC1C(COP(O)(O)=O)OC(C1O)N1C=NC=C1NC(O)=O
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
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Aminoimidazole
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Primary amine
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.7 g/LALOGPS
logP-2ALOGPS
logP-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.17ChemAxon
pKa (Strongest Basic)7.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area200.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.16 m³·mol⁻¹ChemAxon
Polarizability28.19 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 > Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP + Phosphate
N5-Carboxyaminoimidazole ribonucleotide > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-Glutamine > imidazole-glycerol phosphate + N5-Carboxyaminoimidazole ribonucleotide + L-Glutamate + Water
5-Aminoimidazole ribonucleotide + Hydrogen carbonate + Adenosine triphosphate > N5-Carboxyaminoimidazole ribonucleotide + Adenosine diphosphate + Phosphate +2 Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP
N5-Carboxyaminoimidazole ribonucleotide + N5-Carboxyaminoimidazole ribonucleotide > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
SMPDB Pathways:
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
KEGG Pathways:Not Available
EcoCyc Pathways:
  • inosine-5'-phosphate biosynthesis I PWY-6123
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1009000000-f52aa11320ddc5de5423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0012-5219000000-c0eed1bce9a15cd855b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9500000000-0581d72177da95af5538View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1009000000-67b123b7d315754fbcf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9020000000-bb29957fea4db103eb81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59eb08da2b3176098f8cView in MoNA
References
References:
  • Firestine, S. M., Poon, S. W., Mueller, E. J., Stubbe, J., Davisson, V. J. (1994). "Reactions catalyzed by 5-aminoimidazole ribonucleotide carboxylases from Escherichia coli and Gallus gallus: a case for divergent catalytic mechanisms." Biochemistry 33:11927-11934. Pubmed: 7918411
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB12268
Pubchem Compound ID656466
Kegg IDNot Available
ChemSpider ID570854
Wikipedia IDNot Available
BioCyc IDCPD0-181
EcoCyc IDCPD0-181

Enzymes

Protein Details
1. Phosphoribosylaminoimidazole carboxylase ATPase subunit
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.
Protein Details
2. Phosphoribosylaminoimidazole carboxylase catalytic subunit
General function:
Involved in 5-(carboxyamino)imidazole ribonucleotide mutase activity
Specific function:
This subunit can alone transform AIR to CAIR, but in association with purK, which possesses an ATPase activity, an enzyme complex is produced which is capable of converting AIR to CAIR efficiently under physiological condition
Gene Name:
purE
Uniprot ID:
P0AG18
Molecular weight:
17780
Reactions
5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole = 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate.
Protein Details
3. Imidazole glycerol phosphate synthase subunit hisH
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisH subunit provides the glutamine amidotransferase activity that produces the ammonia necessary to hisF for the synthesis of IGP and AICAR
Gene Name:
hisH
Uniprot ID:
P60595
Molecular weight:
21653
Reactions
5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-glutamine = imidazole-glycerol phosphate + 5-aminoimidazol-4-carboxamide ribonucleotide + L-glutamate + H(2)O.
Protein Details
4. Imidazole glycerol phosphate synthase subunit hisF
General function:
Involved in catalytic activity
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisF subunit catalyzes the cyclization activity that produces IGP and AICAR from PRFAR using the ammonia provided by the hisH subunit
Gene Name:
hisF
Uniprot ID:
P60664
Molecular weight:
28454
Reactions
5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-glutamine = imidazole-glycerol phosphate + 5-aminoimidazol-4-carboxamide ribonucleotide + L-glutamate + H(2)O.