Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 14:21:33 -0600
Update Date	2015-06-03 17:19:04 -0600
Secondary Accession Numbers	ECMDB12278
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaddcf5c0> Close
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
Weight:	Average: 577.331 Monoisotopic: 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
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Imidazole ribonucleosides and ribonucleotides
Sub Class	1-ribosyl-imidazolecarboxamides
Direct Parent	1-ribosyl-imidazolecarboxamides
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates 2-heteroaryl carboxamides Carbonylimidazoles Monoalkyl phosphates Beta-hydroxy ketones Acyloins N-substituted imidazoles Alpha-hydroxy ketones Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Primary carboxylic acid amides Secondary alcohols Azacyclic compounds Formamidines Carboxamidines Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides
Substituents	1-ribosyl-imidazolecarboxamide Pentose-5-phosphate Pentose phosphate Glycosyl compound N-glycosyl compound Pentose monosaccharide Monosaccharide phosphate 2-heteroaryl carboxamide Monoalkyl phosphate Imidazole-4-carbonyl group Organic phosphoric acid derivative Alkyl phosphate Beta-hydroxy ketone Acyloin Phosphoric acid ester N-substituted imidazole Monosaccharide Alpha-hydroxy ketone Azole Imidazole Heteroaromatic compound Vinylogous amide Tetrahydrofuran Secondary alcohol Primary carboxylic acid amide Carboxamide group Ketone Oxacycle Organoheterocyclic compound Propargyl-type 1,3-dipolar organic compound Azacycle Organic 1,3-dipolar compound Amidine Carboxylic acid derivative Formamidine Carboxylic acid amidine Organooxygen compound Organopnictogen compound Carbonyl group Organic oxygen compound Organic oxide Hydrocarbon derivative Alcohol Organic nitrogen compound Organonitrogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.21 g/L ALOGPS logP -2 ALOGPS logP -5.7 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.3 ChemAxon pKa (Strongest Basic) 7.35 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 326.04 Ų ChemAxon Rotatable Bond Count 13 ChemAxon Refractivity 116.21 m³·mol⁻¹ ChemAxon Polarizability 48.23 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR PhosphoribosylformiminoAICAR-phosphate > Phosphoribulosylformimino-AICAR-P Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P
SMPDB Pathways:	Secondary Metabolites: Histidine biosynthesis PW000984 histidine biosynthesis PW000810
KEGG Pathways:	Histidine metabolism ec00340 Metabolic pathways eco01100
EcoCyc Pathways:	histidine biosynthesis HISTSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-052b-8903320000-c6b662cea35d9d9398bb View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-001m-9802376000-4e0678746bfb4b789df7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0129250000-34da0f09334273bb5733 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-1749000000-35b2fd0c7ba2bf365cc0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-1953000000-905c7e021fac249fd064 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01t9-9677450000-0060eff9af2626729618 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9211000000-6721677e2439e38c5466 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-b9e22a6bd0b38386b60d View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID HMDB12278 Pubchem Compound ID 1013 Kegg ID C04916 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID PHOSPHORIBULOSYL-FORMIMINO-AICAR-P EcoCyc ID PHOSPHORIBULOSYL-FORMIMINO-AICAR-P

Enzymes