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Identification
YMDB IDYMDB00417
Name1-(5-phospho-D-ribosyl)-5-[(5-phospho-D-ribosylamino)methylideneamino]imidazole-4-carboxamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide, also known as N-(5'-phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide or phosphoribosyl-formimino-aicar-phosphate, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide is a very strong basic compound (based on its pKa). 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • 1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide
  • 5-(5-phospho-D-ribosylaminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide
  • N-(5'-phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
  • N-(5'-phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide
  • N-(5'-phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
  • N-(5'-phosphoribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
  • Phosphoribosyl-formimino-AICAR-phosphate
  • 5'-ProFAR
  • 1-(5-Phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide
  • Phosphoribosyl-formimino-aicar-phosphoric acid
  • 1-(5-Phospho-b-D-ribosyl)-5-[(5-phospho-b-D-ribosylamino)methylideneamino]imidazole-4-carboxamide
  • 1-(5-Phospho-β-D-ribosyl)-5-[(5-phospho-β-D-ribosylamino)methylideneamino]imidazole-4-carboxamide
  • 1-(5-O-Phosphono-beta-D-ribofuranosyl)-5-[[[(5-O-phosphono-beta-D-ribofuranosyl)amino]methylene]amino]-1H-imidazole-4-carboxamide
  • 1-(5-O-Phosphono-β-D-ribofuranosyl)-5-[[[(5-O-phosphono-β-D-ribofuranosyl)amino]methylene]amino]-1H-imidazole-4-carboxamide
  • 5-(5'-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide
  • 5-(5-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamide
  • 5-(5’-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide
  • N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolylcarboxamide
  • N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phospho-D-ribosyl)-4-imidazolecarboxamide
  • N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolecarboxamide
  • N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolylcarboxamide
  • N-(5’-Phosphoribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolecarboxamide
  • N-5-Phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotide
  • Phosphoribosyl-formimino-AICAR-P
  • PhosphoribosylformiminoAICAR-phosphate
CAS numberNot Available
WeightAverage: 577.331
Monoisotopic: 577.082238179
InChI KeyQOUSHGMTBIIAHR-KEOHHSTQSA-N
InChIInChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(N'-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(N'-{5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
Chemical FormulaC15H25N5O15P2
SMILESO[C@H]1[C@@H](O)[C@H](N\C=N\C2=C(C(=O)N)N=CN2[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)O[C@@H]1COP(=O)(O)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Formamidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Amidine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.75 g/LALOGPS
logP-1.8ALOGPS
logP-5.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area318.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity114.57 m³·mol⁻¹ChemAxon
Polarizability48.64 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Histidine metabolismec00340 Map00340
SMPDB ReactionsNot Available
KEGG Reactions
1-(5-phospho-D-ribosyl)-5-[(5-phospho-D-ribosylamino)methylideneamino]imidazole-4-carboxamide5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
1-(5-phosphoribosyl)-5'-AMP + water1-(5-phospho-D-ribosyl)-5-[(5-phospho-D-ribosylamino)methylideneamino]imidazole-4-carboxamide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0229130000-77ae7326f3b61ac79629JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-0729000000-f68502ca665d560b4babJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0796000000-bf5a600e9f63aa3731fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01tc-6419340000-e587f8a52b28fa93d93eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9303000000-becf2ce868f0d12c63f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a4eaaeca4343c1c85295JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u0-0025960000-2cc9b28e3193b926feb6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-0019800000-d29c5701007b716cddd0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3148900000-e0f06be301d6253445e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000070000-a9b419f8601ba73009feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a3ddbffe59a79724cf9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-bcb1b6a36484ebb4bab4JSpectraViewer
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
  • 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 ID18302
HMDB IDHMDB0012277
Pubchem Compound ID9548599
Kegg IDC04896
ChemSpider ID7827522
FOODB IDFDB028909
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
1-(5-phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5- ((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5- phosphoribosyl)imidazole-4-carboxamide
Gene Name:
HIS6
Uniprot ID:
P40545
Molecular weight:
29556.40039
Reactions
1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide → 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide.
General function:
Involved in oxidoreductase activity
Specific function:
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5- phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Gene Name:
HIS4
Uniprot ID:
P00815
Molecular weight:
87720.5
Reactions
1-(5-phosphoribosyl)-AMP + H(2)O → 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
1-(5-phosphoribosyl)-ATP + H(2)O → 1-(5-phosphoribosyl)-AMP + diphosphate.
L-histidinol + H(2)O + 2 NAD(+) → L-histidine + 2 NADH.