Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000838
Identification
Name: Phosphoribulosylformimino-AICAR-P
Description:Phosphoribulosylformimino-aicar-p 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. PRFAR is catalyzed by imidazole glycerol phosphate syntahse. Imidazole glycerol phosphate (IGP) synthase is a glutamine amidotransferase that catalyzes the formation of IGP and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) from N(1)-[(5'-phosphoribulosyl)formimino]-5-aminoimidazole-4-car boxamide ribonucleotide (PRFAR). (PMID 10733892). 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide is an intermediate in the histidine biosynthesis pathway. It is a substrate for the enzyme 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase which catalyzes the reaction 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide.
Structure
Thumb
Synonyms:
  • 5-[(5-Phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide
  • N-(5'-Phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
  • N-(5'Phospho-D-1'-ribulosylformimino)-5-amino-1-(5-phosphoribosyl)-4-imidazolecarboxamide
  • Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphate
  • Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphoric acid
  • Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphate
  • Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphoric acid
  • Phosphoribulosyl-formimino-aicar-p
  • Phosphoribulosylformiminoaicar-phosphate
  • Phosphoribulosylformiminoaicar-phosphoric acid
  • Prfar
  • PRuFAP
Chemical Formula: C15H25N5O15P2
Average Molecular Weight: 577.331
Monoisotopic Molecular Weight: 577.082238179
InChI Key: BLKFNHOCHNCLII-IIZOACFYSA-N
InChI:InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/t7-,8+,10+,11+,12+,15+/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3R)-5-[(E)-N'-{4-carbamoyl-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Name: [(2R,3R)-5-[(E)-N'-{5-carbamoyl-3-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxyphosphonic acid
SMILES:O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide 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-ribosyl-imidazolecarboxamides
Direct Parent 1-phosphoribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-phosphoribosyl-imidazolecarboxamide
  • 1-phosphoribosyl-imidazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Aminoimidazole
  • Acyloin
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Alpha-hydroxy ketone
  • Alpha-aminoketone
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketone
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.21 mg/mLALOGPS
logP-2ALOGPS
logP-5.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)7.35ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area326.04 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity116.21 m3·mol-1ChemAxon
Polarizability48.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129250000-34da0f09334273bb5733View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1749000000-35b2fd0c7ba2bf365cc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1953000000-905c7e021fac249fd064View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-9677450000-0060eff9af2626729618View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9211000000-6721677e2439e38c5466View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b9e22a6bd0b38386b60dView in MoNA
References
References:
  • Chittur, S. V., Chen, Y., Davisson, V. J. (2000). "Expression and purification of imidazole glycerol phosphate synthase from Saccharomyces cerevisiae." Protein Expr Purif 18:366-377. Pubmed: 10733892
  • 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 IDHMDB12278
Pubchem Compound ID1013
Kegg IDC04916
ChemSpider ID30776607
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBULOSYL-FORMIMINO-AICAR-P
EcoCyc IDPHOSPHORIBULOSYL-FORMIMINO-AICAR-P