Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000220
Identification
Name: Phosphoribosylformylglycineamidine
Description:5-Phosphoribosyl-n-formylglycineamidine is part of the 5-aminoimidazole ribonucleotide biosynthesis pathway. 5-amino-1-(5-phospho-D-ribosyl)imidazole (AIR) is a key intermediate in the biosynthesis of purine nocleotides and thiamine. It is synthesized from 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) in 5 steps, catalyzed by the enzymes amidophosphoribosyl transferase, phosphoribosylamine-glycine ligase, phosphoribosylglycinamide formyltransferase, phosphoribosylformylglycinamide synthetase and phosphoribosylformylglycinamide cyclo-ligase.
Structure
Thumb
Synonyms:
  • 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine
  • 5'-phosphoribosyl-N-formyl glycineamidine
  • 5'-Phosphoribosyl-N-formyl glycineamidine
  • 5'-Phosphoribosylformylglycinamidine
  • 5-Phosphoribosyl-N-formylglycineamidine
  • FGAM
  • N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-b-D-ribofuranosyl)-Formamide
  • N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-delta-ribofuranosyl)-formamide
  • N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-δ-ribofuranosyl)-formamide
  • N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-delta-ribofuranosyl)-Formamide
  • N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-β-δ-ribofuranosyl)-formamide
Chemical Formula: C8H16N3O8P
Average Molecular Weight: 313.2017
Monoisotopic Molecular Weight: 313.067501015
InChI Key: PMCOGCVKOAOZQM-XVFCMESISA-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: 37721-04-3
IUPAC Name:{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxyphosphonic acid
SMILES:O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.65 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.72 m3·mol-1ChemAxon
Polarizability25.96 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
References
References:
  • Jayaram HN, Lui MS, Plowman J, Pillwein K, Reardon MA, Elliott WL, Weber G: Oncolytic activity and mechanism of action of a novel L-cysteine derivative, L-cysteine, ethyl ester, S-(N-methylcarbamate) monohydrochloride. Cancer Chemother Pharmacol. 1990;26(2):88-92. Pubmed: 2347042
  • 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
  • Maegawa T, Karasawa T, Ohta T, Wang X, Kato H, Hayashi H, Nakamura S: Linkage between toxin production and purine biosynthesis in Clostridium difficile. J Med Microbiol. 2002 Jan;51(1):34-41. Pubmed: 11800470
  • 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 ID18413
HMDB IDHMDB00999
Pubchem Compound ID154
Kegg IDC04640
ChemSpider ID7830994
Wikipedia IDNot Available
BioCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
EcoCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE