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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2021-09-14 15:39:01 UTC
HMDB IDHMDB0002305
Secondary Accession Numbers
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
Thumb
Synonyms
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDNot Available
Good Scents IDNot Available
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