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Identification
YMDB IDYMDB00077
Name5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid, also known as 1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxylate, 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. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid.
Structure
Thumb
Synonyms
  • 1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylate
  • 1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylate
  • 4-Carboxy-5-aminoimidazole ribonucleotide
  • 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
  • 5-amino-4-carboxyimidazole ribonucleotide
  • 5-Amino-4-imidazolecarboxylic acid ribonucleotide
  • 5-Aminoimidazole carboxilic acid ribonucleotice
  • 5-Aminoimidazole-4-carboxilic acid ribonucleotide
  • 5'-Phosphoribosyl-4-carboxy-5-aminoimidazole
  • 5'-Phosphoribosyl-5-amino-4-imidazolecarboxylate
  • 5'Phosphoribosyl-4-carboxy-5-aminoimidazole
  • Carboxyaminoimidazole ribonucleotide
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acid
  • 1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid
  • 5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acid
  • Carboxy-AIR
  • AICOR
  • Carboxyaminoimidazole ribotide
  • CAIR
  • 5-Amino-1-(5-O-phosphonopentofuranosyl)-1H-imidazole-4-carboxylic acid
  • 1-(5’-Phosphoribosyl)-4-carboxy-5-aminoimidazole
  • 1-(5’-Phosphoribosyl)-5-amino-4-carboxyimidazole
  • 1-(5’-Phosphoribosyl)-5-amino-4-imidazolecarboxylate
  • 5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid
  • 5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid
  • 5-Aminoimidazole 4-carboxylic acid ribonucleotide
  • 5-Aminoimidazolecarboxylic acid ribonucleotide
  • 5’-Phosphoribosyl-4-carboxy-5-aminoimidazole
  • 5’-Phosphoribosyl-5-amino-4-imidazolecarboxylate
CAS number6001-14-5
WeightAverage: 339.1959
Monoisotopic: 339.046765573
InChI KeyXFVULMDJZXYMSG-ZIYNGMLESA-N
InChIInChI=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
IUPAC Name5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid
Traditional IUPAC Name5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid
Chemical FormulaC9H14N3O9P
SMILES[H]OC(=O)C1=C(N([H])[H])N(C([H])=N1)[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]
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
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Imidazole-4-carbonyl group
  • Alkyl phosphate
  • Phosphoric acid ester
  • Aminoimidazole
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Azole
  • Vinylogous amide
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Primary amine
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.81 g/LALOGPS
logP-2ALOGPS
logP-3.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)7.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area197.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.32 m³·mol⁻¹ChemAxon
Polarizability28.49 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
N5-Carboxyaminoimidazole ribonucleotide5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphateSAICAR + phosphate + ADP + hydron
KEGG Reactions
5-Aminoimidazole ribonucleotide + Carbon dioxide5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + hydron
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphateSAICAR + phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9613000000-2a087bcb710ee7b50b52JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00lu-2923230000-25e41df497cf1b5c9281JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-87d6bac417ced888900fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-e298883e772e11c253f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8900000000-82583bffa17f1262d918JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-8928000000-d296c2812c7b06149794JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-76793052d8d2699d70ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a8b367167e97f6df3690JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0539000000-deee029059e464053ab9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-c7cafadad92d61fbb8a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01u0-7900000000-97962f3ed9f96ac07b6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3009000000-ff79299d0fd8156f9b05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a211e114c93b066eaf36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-bfdd206a6413421623edJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28413
HMDB IDHMDB06273
Pubchem Compound ID165388
Kegg IDC04751
ChemSpider ID144983
FOODB IDFDB023871
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE

Enzymes

General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxylate = 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2)
Gene Name:
ADE2
Uniprot ID:
P21264
Molecular weight:
62338.69922
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2).
General function:
Involved in ATP binding
Specific function:
ATP + 5-amino-1-(5-phospho-D- ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido)succinate
Gene Name:
ADE1
Uniprot ID:
P27616
Molecular weight:
34603.10156
Reactions
ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate → ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate.