Record Information
Version2.0
Creation Date2012-05-31 13:49:35 -0600
Update Date2015-06-03 15:53:55 -0600
Secondary Accession Numbers
  • ECMDB01308
Identification
Name:5'-Phosphoribosyl-N-formylglycineamide
Description5'-Phosphoribosyl-N-formylglycineamide (also known as FGAR or N-Formyl-GAR) is a substrate for Phosphoribosylformylglycinamidine synthase. It is involved in aminoimidazole ribonucleotide biosynthesis and plays a vital role in purine metabolism as well as the conversion of glutamine to glutamate. 5'-Phosphoribosyl-N-formylglycineamide is described as a glycinamide ribonucleotide having a phosphate group at the 5-position and a formyl group on the glycine nitrogen.
Structure
Thumb
Synonyms:
  • 5'-P-ribosyl-N-formylglycineamide
  • 5'-P-Ribosyl-N-formylglycineamide
  • 5'-phosphoribosyl-N-formylglycinamide
  • 5'-Phosphoribosyl-formylglycinamide
  • 5'-Phosphoribosyl-N-formylglycinamide
  • 5'-Phosphoribosyl-N-formylglycineamide
  • 5-phosphoribosyl-N-formalglycineamide
  • 5-Phosphoribosyl-N-formalglycineamide
  • FGAR
  • N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide
  • N-Formyl-GAR
  • N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide
Chemical Formula:C8H15N2O9P
Weight:Average: 314.1865
Monoisotopic: 314.0515166
InChI Key:VDXLUNDMVKSKHO-XVFCMESISA-N
InChI:InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxyphosphonic acid
SMILES:O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassGlycinamide ribonucleotides
Sub ClassNot Available
Direct ParentGlycinamide ribonucleotides
Alternative Parents
Substituents
  • Glycinamide-ribonucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-formyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-formyl-alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Monosaccharide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Secondary carboxylic acid amide
  • 1,2-diol
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.52 g/LALOGPS
logP-2.3ALOGPS
logP-3.9ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.25 m³·mol⁻¹ChemAxon
Polarizability25.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Formic acid + Glycineamideribotide > ADP + 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Phosphate
N10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate
N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide
Glycineamideribotide + 5,10-Methenyltetrahydrofolate + Water <> 5'-Phosphoribosyl-N-formylglycineamide + Tetrahydrofolic acid
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate
Formic acid + Adenosine triphosphate + 5'-Phospho-ribosylglycinamide > 5'-Phosphoribosyl-N-formylglycineamide + ADP + Pyrophosphate
Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + Glycineamideribotide
Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + Glycineamideribotide
N1-(5-phospho-β-D-ribosyl)glycinamide + Adenosine triphosphate + Formic acid > 5'-Phosphoribosyl-N-formylglycinamide + Adenosine diphosphate + Phosphate + Hydrogen ion + 5'-Phosphoribosyl-N-formylglycineamide + ADP
5'-Phosphoribosyl-N-formylglycinamide + Water + L-Glutamine + Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide > 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + Phosphate + Adenosine diphosphate + Hydrogen ion + L-Glutamate + ADP
10-formyl-tetrahydrofolate mono-L-glutamate + N1-(5-phospho-β-D-ribosyl)glycinamide > Hydrogen ion + tetrahydropteroyl mono-L-glutamate + 5'-Phosphoribosyl-N-formylglycineamide
N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
Adenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate
N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
Adenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate
SMPDB Pathways:
One Carbon Pool by Folate IPW001735 ThumbThumb?image type=greyscaleThumb?image type=simple
One carbon pool by folatePW000773 ThumbThumb?image type=greyscaleThumb?image type=simple
Thiamin diphosphate biosynthesisPW002028 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121
  • 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122
  • superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277
  • tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate PWY-6613
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9330000000-47bd3a51454a22349c16View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-5972200000-28cbe677e79c994d5692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9121000000-70e7f7e392d67c9062d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9110000000-24b14d3360fd37fa0b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-6c2f243f9e36f7267013View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01r6-8914000000-411b5cf47e3e7e5511fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-fc9464d8ad7b3b1ac820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ccc93e5e04249a7f1425View in MoNA
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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB01308
Pubchem Compound ID130805
Kegg IDC04376
ChemSpider ID146
Wikipedia IDNot Available
BioCyc ID5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE
EcoCyc ID5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE
Ligand ExpoFGR

Enzymes

General function:
Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:
10-formyltetrahydrofolate + N(1)-(5-phospho-D- ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5- phospho-D-ribosyl)glycinamide
Gene Name:
purN
Uniprot ID:
P08179
Molecular weight:
23238
Reactions
10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide.
General function:
Involved in catalytic activity
Specific function:
ATP + N(2)-formyl-N(1)-(5-phospho-D- ribosyl)glycinamide + L-glutamine + H(2)O = ADP + phosphate + 2- (formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-glutamate
Gene Name:
purL
Uniprot ID:
P15254
Molecular weight:
141402
Reactions
ATP + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide + L-glutamine + H(2)O = ADP + phosphate + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-glutamate.
General function:
Involved in ATP binding
Specific function:
Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:
purT
Uniprot ID:
P33221
Molecular weight:
42433
Reactions
Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.