2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine (BioCAD00000002243)

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Metabolite Card

Formula: C8H16N3O8P (313.0675)
SMILES: O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O

Synonyms [en]

2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine; 2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine; 5'-Phosphoribosyl-N-formylglycinamidine; 1-(5'-Phosphoribosyl)-N-formylglycinamidine; 5'-phosphoribosylformylglycinamidine; Phosphoribosylformylglycineamidine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000002243). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5'-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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 6157-85-3
  • PubChem: 440417
  • PubChem: 5462266
  • ChEBI: ChEBI:18413
  • ChEBI: ChEBI:190761
  • HMDB: HMDB0000999
  • HMDB: HMDB0002305
  • HMDB: HMDB06211
  • KEGG: C04640
  • BioCyc: 5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
  • Wikipedia: 5%E2%80%B2-Phosphoribosylformylglycinamidine
  • RefMet: RM0071784
  • Metlin: METLIN_3442
  • Coconut NaturalProduct: CNP0083578.0
  • Coconut NaturalProduct: CNP0540722.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R04208 6.3.3.1 2-(formamido)-N1-(5-phosphoribosyl)acetamidine cyclo-ligase (ADP-forming)
KEGG:R04463 6.3.5.3 5'-phosphoribosylformylglycinamide:L-glutamine amido-ligase (ADP-forming)
BioCyc:AIRS-RXN 6.3.3.1 ATP + 5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE --> PROTON + ADP + Pi + 5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE
BioCyc:FGAMSYN-RXN 6.3.5.3 ATP + 5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE + GLN + WATER --> PROTON + GLT + ADP + Pi + 5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
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Organism Source

Taxonomy Source

  1. Citrullus lanatus [ncbi taxid: 3654]
  2. Escherichia coli [ncbi taxid: 562]
  3. Homo sapiens [ncbi taxid: 9606]
  4. Mus musculus [ncbi taxid: 10090]
  5. Saccharomyces cerevisiae [ncbi taxid: 4932]

Pathway Synthetic

pathway id name
BioCyc:CAULONA1000_PWY-841 purine nucleotides de novo biosynthesis II
BioCyc:CALBI_PRPP-PWY superpathway of histidine, purine and pyrimidine biosynthesis
BioCyc:CALBI_DENOVOPURINE2-PWY purine nucleotides de novo biosynthesis
BioCyc:CAULONA1000_PWY-6121 5-aminoimidazole ribonucleotide biosynthesis I
PathBank:SMP0120670 Adenylosuccinate Lyase Deficiency
PathBank:SMP0120448 Adenosine Deaminase Deficiency
PathBank:SMP0120452 AICA-Ribosiduria
PathBank:SMP0120508 Lesch-Nyhan Syndrome (LNS)
PathBank:SMP0120532 Molybdenum Cofactor Deficiency
PathBank:SMP0120536 Purine Nucleoside Phosphorylase Deficiency
PathBank:SMP0120577 Xanthinuria Type I
PathBank:SMP0120601 Mitochondrial DNA Depletion Syndrome
PathBank:SMP0000167 Adenylosuccinate Lyase Deficiency
PathBank:SMP0000220 Xanthine Dehydrogenase Deficiency (Xanthinuria)
PathBank:SMP0000512 Xanthinuria Type I
PathBank:SMP0000536 Mitochondrial DNA Depletion Syndrome-3
PathBank:SMP0063668 Purine Metabolism
PathBank:SMP0120669 Adenosine Deaminase Deficiency
PathBank:SMP0120673 AICA-Ribosiduria
PathBank:SMP0120709 Gout or Kelley-Seegmiller Syndrome
View All Pathways