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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2020-04-08 21:24:43 UTC
HMDB IDHMDB0002305
Secondary Accession Numbers
  • HMDB0006211
  • HMDB0062650
  • HMDB02305
  • HMDB06211
  • HMDB62650
Metabolite Identification
Common Name5'-Phosphoribosyl-N-formylglycinamidine
Description5'-Phosphoribosyl-N-formylglycinamidine, also known as FGAM or phosphoribosylformylglycinamidine, 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. FGAM is a very strong basic compound (based on its pKa). Within humans, FGAM participates in several enzymatic reactions. FGAM is an intermediate in purine metabolism and it can be biosynthesized (along with L-glutamic acid) from 5'-phosphoribosyl-N-formylglycinamide (FGAR) and L-glutamine. This reaction is catalyzed by the enzyme phosphoribosylformylglycinamidine synthase (EC 6.3.5.3). Additionally, FGAM can be converted into aminoimidazole ribotide (AIR) through its interaction with the enzyme trifunctional purine biosynthetic protein adenosine-3 (EC 6.3.3.1). Outside of the human body, FGAM has been detected, but not quantified in, several different foods, such as Welsh onions, green beans, chicories, European cranberries, and Mexican oregano. This could make FGAM a potential biomarker for the consumption of these foods.
Structure
Data?1586381083
Synonyms
ValueSource
1-(5'-Phosphoribosyl)-N-formylglycinamidineKegg
5'-PhosphoribosylformylglycinamidineKegg
2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidineKegg
5'-Phosphoribosyl-N-formyl glycineamidineHMDB
FGAMHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-b-D-ribofuranosyl)-formamideHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-delta-ribofuranosyl)-formamideHMDB
1-(5’-phosphoribosyl)-N-formylglycinamidineHMDB
2-(Formamido)-N1-(5'-phosphoribosyl)acetamidineHMDB
2-(Formamido)-N1-(5’-phosphoribosyl)acetamidineHMDB
2-Formamido-N(1)-(5-O-phosphonato-D-ribosyl)acetamidineHMDB
5'-Phosphoribosyl-alpha-N-formylglycineamidineHMDB
5'-Phosphoribosyl-α-N-formylglycineamidineHMDB
5’-phosphoribosyl-N-formyl glycineamidineHMDB
5’-phosphoribosyl-N-formylglycinamidineHMDB
5’-phosphoribosyl-α-N-formylglycineamidineHMDB
5’-phosphoribosylformylglycinamidineHMDB
N-[2-Imino-2-[(5-O-phosphono-beta-D-ribofuranosyl)amino]ethyl]formamideHMDB
N-[2-Imino-2-[(5-O-phosphono-β-D-ribofuranosyl)amino]ethyl]formamideHMDB
PhosphoribosylformylglycineamidineHMDB
Formylglycinamidine ribonucleotideHMDB
PhosphoribosylformylglycinamidineHMDB
5'-Phosphoribosyl-N-formylglycinamidineKEGG
Chemical FormulaC8H16N3O8P
Average Molecular Weight313.2017
Monoisotopic Molecular Weight313.067501015
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number6157-85-3
SMILES
O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O
InChI Identifier
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
InChI KeyPMCOGCVKOAOZQM-XVFCMESISA-N
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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.4 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
Polarizability25.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9860000000-053d3def2f2031f6f985Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03fv-9626200000-4af28dfe3b4dc1c71a02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-9732000000-7a823a35c9828d22327cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9300000000-2f206fd034f1fb2795fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmr-9400000000-a855d87bf0ed7c457172Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2c-6903000000-621c45a21326a0c06addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0415faa4289f87539ce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73ad9c3af703650a3eedSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022360
KNApSAcK IDNot Available
Chemspider ID7830994
KEGG Compound IDC04640
BioCyc ID5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5930
PubChem Compound440417
PDB IDNot Available
ChEBI ID18413
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295