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5'-Phosphoribosyl-N-formylglycinamide (YMDB00001)

Identification
YMDB IDYMDB00001
Name5'-Phosphoribosyl-N-formylglycinamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5'-Phosphoribosyl-N-formylglycineamide (FGAR or N-Formyl-GAR) is a glycinamide ribonucleotide having a phosphate group at the 5-position and a formyl group on the glycine nitrogen. FGAR is a substrate for phosphoribosylformylglycinamidine synthase and phosphoribosylglycinamide formyltransferase. It is involved in aminoimidazole ribonucleotide biosynthesis and plays a vital role in de novo purine synthesis as well as tetrahydrofolate synthesis. It also plays a role in the conversion of glutamine to glutamate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 5-phosphoribosyl-N-formalglycineamide
  • 5'-P-ribosyl-N-formylglycineamide
  • 5'-phosphoribosyl-formylglycinamide
  • 5'-phosphoribosyl-N-formylglycinamide
  • 5'-phosphoribosyl-N-formylglycineamide
  • FGAR
  • Formylglycinamide ribonucleotide
  • Formylglycineamideribotide
  • N-Formyl-GAR
  • N-Formylglycinamide ribonucleotide
  • N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide
  • N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide
  • Phosphoribosyl-N-formylglycineamide
  • 2-(Formylamino)-N-(5-O-phosphono-beta-D-ribofuranosyl)acetamide
  • 2-(Formylamino)-N-(5-O-phosphono-β-D-ribofuranosyl)acetamide
  • 5’-Phosphoribosyl-N-formylglycinamide
  • Formylglycinamide ribotide
  • Phosphoribosylformylglycinamide
  • alpha-N-Formylglycinamide ribonucleotide
  • α-N-Formylglycinamide ribonucleotide
CAS number349-34-8
WeightAverage: 314.1865
Monoisotopic: 314.0515166
InChI KeyVDXLUNDMVKSKHO-XVFCMESISA-N
InChIInChI=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
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
Chemical FormulaC8H15N2O9P
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]1([H])O[H])N([H])C(=O)C([H])([H])N([H])C([H])=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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.25 m³·mol⁻¹ChemAxon
Polarizability25.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
N10-Formyl-THF + 5'-Phosphoribosyl-N-formylglycinamide → Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide
N10-Formyl-THF + 5'-Phosphoribosyl-N-formylglycinamide → Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide
Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide → N10-Formyl-THF + Glycineamideribotide
N1-(5-phospho-β-D-ribosyl)glycinamide + Adenosine triphosphate + Formic acid → 5'-Phosphoribosyl-N-formylglycinamide + ADP + phosphate + hydron
5'-Phosphoribosyl-N-formylglycinamide + water + L-Glutamine + Adenosine triphosphate → 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + phosphate + ADP + hydron
KEGG Reactions
Adenosine triphosphate + water + L-Glutamine + 5'-Phosphoribosyl-N-formylglycinamide → phosphate + L-Glutamic acid + hydron + 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + ADP
N10-Formyl-THF + Glycineamideribotide → 5,6,7,8-Tetrahydrofolic acid + hydron + 5'-Phosphoribosyl-N-formylglycinamide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9330000000-47bd3a51454a22349c16JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-5972200000-28cbe677e79c994d5692JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9121000000-70e7f7e392d67c9062d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9110000000-24b14d3360fd37fa0b5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-6c2f243f9e36f7267013JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01r6-8914000000-411b5cf47e3e7e5511fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-fc9464d8ad7b3b1ac820JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ccc93e5e04249a7f1425JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0079000000-0c457b0a6a5c25c65962JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2920000000-569fd550eacc61a8bd6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-32e3418d15835aba1b7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-9036000000-b8480e9ce9f70df638e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-14698f4417bb19153972JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e93ac01407977ed80740JSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18272
HMDB IDHMDB01308
Pubchem Compound ID151
Kegg IDC04376
ChemSpider ID115687
FOODB IDFDB030552
Wikipedia IDNot Available
BioCyc ID5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE

Enzymes

Protein Details
1. Phosphoribosylformylglycinamidine synthase
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:
ADE6
Uniprot ID:
P38972
Molecular weight:
148904.0
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.
Protein Details
2. Phosphoribosylglycinamide formyltransferase
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:
ADE8
Uniprot ID:
P04161
Molecular weight:
23540.0
Reactions
10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide → tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide.
Protein Details
3. Phosphoribosylaminoimidazole carboxylase
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxylate = 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2)
Gene Name:
ADE2
Uniprot ID:
P21264
Molecular weight:
62338.69922
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2).