ChemFOnt: Showing chemical card for 5'-Phosphoribosyl-N-formylglycinamidine (CFc000001554)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:12 UTC

Chemfont ID

CFc000001554

Molecule Identification

Common Name

5'-Phosphoribosyl-N-formylglycinamidine

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₈H₁₆N₃O₈P

Average Molecular Weight

313.2017

Monoisotopic Molecular Weight

313.067501015

IUPAC Name

({5-[(Z)-(1-amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acid

Traditional Name

{5-[(Z)-(1-amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl}methoxyphosphonic acid

CAS Registry Number

6157-85-3

SMILES

OC=NCC(=N)NC1OC(COP(O)(O)=O)C(O)C1O

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)

InChI Key

PMCOGCVKOAOZQM-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0002305)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

One Carbon Pool by Folate (PathBank: SMP0122040)
One Carbon Pool by Folate I (PathBank: SMP0002369)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.58 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.93 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.43 m³·mol⁻¹	ChemAxon
Polarizability	27.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062650

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022957

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5'-Phosphoribosyl-N-formylglycinamidine (CFc000001554)

MOL for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

3D MOL for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

3D SDF for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

3D-SDF for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

PDB for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

3D PDB for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

SMILES for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

INCHI for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

Structure for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)

3D Structure for CFc000001554 (5'-Phosphoribosyl-N-formylglycinamidine)