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Identification
YMDB IDYMDB00758
Name2-formamido-N(1)-(5-phospho-D-ribosyl)acetamidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-formamido-N(1)-(5-phospho-D-ribosyl)acetamidine, also known as 1-(5'-phosphoribosyl)-N-formylglycinamidine, 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. 2-formamido-N(1)-(5-phospho-D-ribosyl)acetamidine is a very strong basic compound (based on its pKa). 2-formamido-N(1)-(5-phospho-D-ribosyl)acetamidine exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 1-(5-phosphoribosyl)-n-formylglycinamidine
  • 1-(5'-Phosphoribosyl)-N-formylglycinamidine
  • 2-(formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine
  • 2-(formamido)-N(1)-(5'-phosphoribosyl)acetamidine
  • 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine
  • 2-(formamido)-n1-(5-phosphoribosyl)acetamidine
  • 2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine
  • 5-phosphoribosyl-n-formylglycinamidine
  • 5-phosphoribosylformylglycinamidine
  • 5'-Phosphoribosyl-N-formylglycinamidine
  • 5'-Phosphoribosylformylglycinamidine
  • FGAM
CAS number6157-85-3
WeightAverage: 313.2017
Monoisotopic: 313.067501015
InChI KeyPMCOGCVKOAOZQM-ZRTZXPPTSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,4R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC NameFGAM
Chemical FormulaC8H16N3O8P
SMILESO[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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-7950000000-52597db3064d3890b1d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-9732000000-7a823a35c9828d22327cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9300000000-2f206fd034f1fb2795fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmr-9400000000-a855d87bf0ed7c457172JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2c-6903000000-621c45a21326a0c06addJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0415faa4289f87539ce2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73ad9c3af703650a3eedJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Tret'iakov, O. I. u., Ryzhova, T. A., Velichutina, I. V., Kostikova, T. R., Miasnikov, A. N., Smirnov, M. N., Domkin, V. D. (1995). "[Glycine amide ribonucleotide synthetase (EC 6.3.4.13)--is aminoimidazole ribonucleotide synthetase (EC 6.3.3.1) from Saccharomyces cerevisiae]." Biokhimiia 60:2011-2021.8600995
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18413
HMDB IDHMDB06211
Pubchem Compound ID9552078
Kegg IDC04640
ChemSpider ID21864854
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE

Enzymes

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.
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.