5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (PAMDB000663)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000663
Identification
Name: 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
Description:5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21].
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazole carboxylate
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazole carboxylic acid
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylate
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acid
  • 1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylate
  • 1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid
  • 1-(5-Phosphoribosyl)-4-carboxy-5-aminoimidazole
  • 4-Carboxy-5-aminoimidazole ribonucleotide
  • 4-Carboxyaminoimidazole ribonucleotide
  • 5'-P-Ribosyl-4-carboxy-5-aminoimidazole
  • 5'-Phosphoribosyl-4-carboxy-5-aminoimidazole
  • 5'-Phosphoribosyl-5-amino-4-imidazolecarboxylate
  • 5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acid
  • 5'Phosphoribosyl-4-carboxy-5-aminoimidazole
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
  • 5-Amino-4-carboxyimidazole ribonucleotide
  • 5-Amino-4-imidazolecarboxylate ribonucleotide
  • 5-Amino-4-imidazolecarboxylic acid ribonucleotide
  • 5-Aminoimidazole carboxilate ribonucleotice
  • 5-Aminoimidazole carboxilic acid ribonucleotice
  • 5-Aminoimidazole-4-carboxilate ribonucleotide
  • 5-Aminoimidazole-4-carboxilic acid ribonucleotide
  • 5-Phosphoribosyl-4-carboxy-5-aminoimidazole
  • CAIR
  • Carboxyaminoimidazole ribonucleotide
  • Phosphoribosyl-carboxy-aminoimidazole
Chemical Formula: C9H14N3O9P
Average Molecular Weight: 339.1959
Monoisotopic Molecular Weight: 339.046765573
InChI Key: XFVULMDJZXYMSG-ZIYNGMLESA-N
InChI:InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1
CAS number: Not Available
IUPAC Name:5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid
Traditional IUPAC Name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid
SMILES:NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(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
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Aminoimidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.81 mg/mLALOGPS
logP-2ALOGPS
logP-3.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.17ChemAxon
pKa (Strongest Basic)7.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area197.59 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.32 m3·mol-1ChemAxon
Polarizability28.52 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Phosphoribosyl-5-carboxyaminoimidazole
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid <> ADP + Phosphate + SAICAR
5-Carboxyamino-1-(5-phospho-D-ribosyl)imidazole + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole <> 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
N5-Carboxyaminoimidazole ribonucleotide > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > ADP + Inorganic phosphate + SAICAR
5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Aminoimidazole ribonucleotide + Carbon dioxide
N5-Carboxyaminoimidazole ribonucleotide + N5-Carboxyaminoimidazole ribonucleotide > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > SAICAR + Phosphate + Adenosine diphosphate + Hydrogen ion + SAICAR + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-87d6bac417ced888900fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-e298883e772e11c253f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8900000000-82583bffa17f1262d918View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-8928000000-d296c2812c7b06149794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-76793052d8d2699d70ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a8b367167e97f6df3690View in MoNA
References
References:
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28413
HMDB IDHMDB06273
Pubchem Compound ID165388
Kegg IDC04751
ChemSpider ID144983
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
EcoCyc IDPHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
Ligand ExpoC2R