PhosphoribosylformiminoAICAR-phosphate (ECMDB12277) (M2MDB000837)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (753)
Record Information
Version2.0
Creation Date2012-05-31 14:21:30 -0600
Update Date2015-06-03 17:19:04 -0600
Secondary Accession Numbers
  • ECMDB12277
Identification
Name:PhosphoribosylformiminoAICAR-phosphate
DescriptionPhosphoribosylformiminoaicar-phosphate is a member of the chemical class known as 1-Phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 5-(5'-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide
  • 5-(5-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamide
  • N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
  • N-5-Phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotide
  • Phosphoribosyl-formimino-aicar-p
  • Phosphoribosylformiminoaicar-p
  • PhosphoribosylformiminoAICAR-phosphate
  • PhosphoribosylformiminoAICAR-phosphoric acid
  • PRFAP
Chemical Formula:C15H25N5O15P2
Weight:Average: 577.331
Monoisotopic: 577.082238179
InChI Key:QOUSHGMTBIIAHR-UHFFFAOYSA-N
InChI:InChI=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)
CAS number:Not Available
IUPAC Name:({5-[(E)-N'-(4-carbamoyl-1-{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:{5-[(E)-N'-(5-carbamoyl-3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxyphosphonic acid
SMILES:NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 2-arylethylamine
  • Aralkylamine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability48.56 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P
Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate
Phosphoribosyl-AMP + Water > PhosphoribosylformiminoAICAR-phosphate
PhosphoribosylformiminoAICAR-phosphate > Phosphoribulosylformimino-AICAR-P
AICAR > PhosphoribosylformiminoAICAR-phosphate
Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate
PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P
SMPDB Pathways:
Secondary Metabolites: Histidine biosynthesisPW000984 ThumbThumb?image type=greyscaleThumb?image type=simple
histidine biosynthesisPW000810 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rb-5203950000-1dd77522ba2f13d4d3fbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05c2-8300967000-9abc77176f81b5e03cbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0229130000-e38179f09b1f68275733View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-0829000000-7451c604ab5b95a8d175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0896000000-cce14401ee652e0b0313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-8419340000-3b620b7917f57a0e379bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9303000000-8fd246c286b64587a307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-28c9f8fc9fcddd0070c1View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB12277
Pubchem Compound ID1012
Kegg IDC04896
ChemSpider ID987
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBOSYL-FORMIMINO-AICAR-P
EcoCyc IDPHOSPHORIBOSYL-FORMIMINO-AICAR-P

Enzymes

Protein Details
1. Histidine biosynthesis bifunctional protein hisIE
General function:
Involved in phosphoribosyl-AMP cyclohydrolase activity
Specific function:
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5- phosphoribosyl)-AMP + diphosphate
Gene Name:
hisI
Uniprot ID:
P06989
Molecular weight:
22756
Reactions
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5-phosphoribosyl)-AMP + diphosphate.
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
Protein Details
2. 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase
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:
hisA
Uniprot ID:
P10371
Molecular weight:
26033
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.