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2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine (YMDB00398)

Identification
YMDB IDYMDB00398
Name2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine, also known as 1-(5'-phosphoribosyl)-N-formylglycinamidine or FGAM, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine is a very strong basic compound (based on its pKa). 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • [(2R,3S,4R,5R)-5-[(1-amino-2-formamido-ethylidene)amino]-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid
  • 1-(5'-Phosphoribosyl)-N-formylglycinamidine
  • 1-deoxy-1-[2-(formamido)acetimidamido]-D-ribofuranose 5-(dihydrogen phosphate)
  • 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine
  • 2-(formamido)-N(1)-(5'-phosphoribosyl)acetamidine
  • 2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine
  • 5'-Phosphoribosyl-N-formylglycinamidine
  • 5'-Phosphoribosylformylglycinamidine
  • FGAM
  • N-[2-(formamido)ethanimidoyl]-5-O-phosphono-D-ribofuranosylamine
CAS number6157-85-3
WeightAverage: 285.1485
Monoisotopic: 285.036200887
InChI KeyOKXISSDNJVDCJE-KKQCNMDGSA-N
InChIInChI=1S/C6H12N3O8P/c7-6(8-1-10)9-4-2(11)3(12)5(16-4)17-18(13,14)15/h1-5,11-12H,(H2,13,14,15)(H3,7,8,9,10)/t2-,3+,4-,5-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(formamidomethanimidoyl)amino]oxolan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(formamidomethanimidoyl)amino]oxolan-2-yl]oxyphosphonic acid
Chemical FormulaC6H12N3O8P
SMILES[H]O[C@]1([H])[C@@]([H])(OP(=O)(O[H])O[H])O[C@@]([H])(N([H])C(=N[H])N([H])C([H])=O)[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • 1,2-diol
  • Guanidine
  • Secondary alcohol
  • Oxacycle
  • Carboximidamide
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.66 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area181.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.23 m³·mol⁻¹ChemAxon
Polarizability22.69 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
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
5'-Phosphoribosyl-N-formylglycinamide + water + L-Glutamine + Adenosine triphosphate → 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + phosphate + ADP + hydron
2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + Adenosine triphosphate → 5-Aminoimidazole ribonucleotide + phosphate + ADP + hydron
KEGG Reactions
Adenosine triphosphate + 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine → 5-Aminoimidazole ribonucleotide + phosphate + hydron + ADP
Adenosine triphosphate + water + L-Glutamine + 5'-Phosphoribosyl-N-formylglycinamide → phosphate + L-Glutamic acid + hydron + 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9420000000-66c2fbdfe6543975b34eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9211100000-8c192eb0e668267ee507JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-9420000000-b3bc27be13e2ee2c7acaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9000000000-28deb081791dc8ddc223JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-9200000000-a89165bc086324c40cbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005i-9320000000-a01fae3be380b9cd9664JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-9000000000-a3f0b5f30c3340cc16d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0a0a81a42aac5cb4abcbJSpectraViewer
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 ID18413
HMDB IDHMDB06211
Pubchem Compound ID9552078
Kegg IDC04640
ChemSpider ID17216355
FOODB IDFDB023837
Wikipedia IDNot Available
BioCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE

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. Bifunctional purine biosynthetic protein ADE5,7
General function:
Involved in catalytic activity
Specific function:
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide
Gene Name:
ADE5
Uniprot ID:
P07244
Molecular weight:
86067.39844
Reactions
ATP + 5-phospho-D-ribosylamine + glycine → ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide.
ATP + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine → ADP + phosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole.