5-Phosphoribosyl-5-carboxyaminoimidazole (PAMDB001587)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001587
Identification
Name: 5-Phosphoribosyl-5-carboxyaminoimidazole
Description:5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole is an intermediate in purine metabolism and IMP biosynthesis via the de novo pathway. It is a substrate of the PurK enzyme which catalyzes the ATP-dependent conversion of 5-aminoimidazole ribonucleotide (AIR) and HCO3- to N5-carboxyaminoimidazole ribonucleotide (N5-CAIR).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 5-Carboxyamino-1-(5-phospho-D-ribosyl)-imidazole
  • 5-phosphoribosyl-5-carboxyaminoimidazole
  • N5-CAIR
  • N5-CAIR
Chemical Formula: C9H11N3O9P
Average Molecular Weight: 336.1721
Monoisotopic Molecular Weight: 336.023290477
InChI Key: JHLXDWGVSYMXPL-UHFFFAOYSA-K
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)/p-3
CAS number: Not Available
IUPAC Name:N-(1-{3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)carbamate
Traditional IUPAC Name: N-(3-{3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl}imidazol-4-yl)carbamate
SMILES:OC1C(O)C(OC1COP([O-])([O-])=O)N1C=NC=C1NC([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazoles. These are organic compounds containing the imidazole ring linked to a ribose phosphate through a 1-2 bond.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Imidazole ribonucleosides and ribonucleotides
Sub Class1-phosphoribosyl-imidazoles
Direct Parent 1-phosphoribosyl-imidazoles
Alternative Parents
Substituents
  • 1-phosphoribosyl-imidazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Aminoimidazole
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Carbamic acid derivative
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.52 mg/mLALOGPS
logP-1.1ALOGPS
logP-3.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)5.83ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area192.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.05 m3·mol-1ChemAxon
Polarizability27.05 Å3ChemAxon
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
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Phosphoribosyl-5-carboxyaminoimidazole
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-59a258785315de737eb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0119000000-3c24b671f00e253952c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000y-7920000000-71a059951733c823f7e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-357eaf776f2045653354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3119000000-a5ab9eda349cf23bb092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9000000000-648a69b10d5145733551View in MoNA
References
References:
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25244287
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-181
EcoCyc IDCPD0-181