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5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (YMDB00077)

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-carboxylate, also known as 1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole or 1-(5-phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid, 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-carboxylate is a very strong basic compound (based on its pKa). 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
  • 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
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-3.8ChemAxon
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.32 m³·mol⁻¹ChemAxon
Polarizability28.52 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 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 → SAICAR + phosphate + ADP + hydron
KEGG Reactions
5-Aminoimidazole ribonucleotide + Carbon dioxide ↔ 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + hydron
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate ↔ SAICAR + 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 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
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

Protein Details
1. Phosphoribosylaminoimidazole carboxylase
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).
Protein Details
2. Phosphoribosylaminoimidazole-succinocarboxamide synthase
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.