2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine (ECMDB23026) (M2MDB003416)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-10-10 12:13:04 -0600
Update Date2015-06-03 17:25:45 -0600
Secondary Accession Numbers
  • ECMDB23026
Identification
Name:2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine
Description2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine is an intermediate in purine metabolism. The enzyme phosphoribosylformylglycinamidine synthase [EC:6.3.5.3] catalyzes the production of this metabolite from N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R,3S,4R)-5-(Z)-(1-amino-2-formamidoethylidene)amino-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphate
  • (2R,3S,4R)-5-(Z)-(1-amino-2-Formamidoethylidene)amino-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphoric acid
  • 1-(5'-Phosphoribosyl)-N-formylglycinamidine
  • 1-deoxy-1-[2-(formamido)acetimidamido]-D-ribofuranose 5-(dihydrogen phosphate)
  • 1-Deoxy-1-[2-(formamido)acetimidamido]-D-ribofuranose 5-(dihydrogen phosphoric acid)
  • 2-(formamido)-N(1)-(5'-phosphoribosyl)acetamidine
  • 2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine
  • 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine
  • 5'-phosphoribosyl-N-formyl glycineamidine
  • 5'-Phosphoribosyl-n-formyl glycineamidine
  • 5'-Phosphoribosyl-N-formylglycinamidine
  • 5'-Phosphoribosylformylglycinamidine
  • FGAM
  • N-(2-Formamidoethanimidoyl)-5-O-phosphono-D-ribofuranosylamine
  • N-[2-(formamido)ethanimidoyl]-5-O-phosphono-D-ribofuranosylamine
  • [(2R,3S,4R,5R)-5-[(1-amino-2-formamido-Ethylidene)amino]-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonate
  • [(2R,3S,4R,5R)-5-[(1-amino-2-formamido-ethylidene)amino]-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid
Chemical Formula:C8H16N3O8P
Weight:Average: 313.2017
Monoisotopic: 313.067501015
InChI Key:PMCOGCVKOAOZQM-ZRTZXPPTSA-N
InChI:InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8?/m1/s1
CAS number:6157-85-3
IUPAC Name:{[(2R,3S,4R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:FGAM
SMILES:O[C@H]1[C@@H](O)C(NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • 1,2-diol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.65 g/LALOGPS
logP-2.6ALOGPS
logP-4.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)7.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area181.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.72 m³·mol⁻¹ChemAxon
Polarizability26.41 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + 5'-phosphoribosyl-N-formylglycinamide + L-Glutamine + Water > ADP + Inorganic phosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-Glutamate
Adenosine triphosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine > ADP + Inorganic phosphate + 5-Aminoimidazole ribonucleotide
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-7950000000-52597db3064d3890b1d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-9732000000-7a823a35c9828d22327cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9300000000-2f206fd034f1fb2795fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmr-9400000000-a855d87bf0ed7c457172View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2c-6903000000-621c45a21326a0c06addView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0415faa4289f87539ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73ad9c3af703650a3eedView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18413
HMDB IDHMDB06211
Pubchem Compound ID22833657
Kegg IDC04640
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
EcoCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE

Enzymes

Protein Details
1. Phosphoribosylformylglycinamidine cyclo-ligase
General function:
Involved in catalytic activity
Specific function:
ATP + 2-(formamido)-N(1)-(5-phospho-D- ribosyl)acetamidine = ADP + phosphate + 5-amino-1-(5-phospho-D- ribosyl)imidazole
Gene Name:
purM
Uniprot ID:
P08178
Molecular weight:
36854
Reactions
ATP + 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine = ADP + phosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole.
Protein Details
2. 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:
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.