P. aeruginosa Metabolome Database: Phosphoribosylformylglycineamidine (PAMDB000220)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000220

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

🔍MOL SDF PDB SMILES InChI View Structure

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 Description

This 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 Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl 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:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.65 mg/mL	ALOGPS
logP	-2.6	ALOGPS
logP	-4.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	7.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	181.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.72 m³·mol^-1	ChemAxon
Polarizability	25.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate
Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + Phosphate + 5-Aminoimidazole ribonucleotide
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate

Pathways:

Metabolic pathways pae01100
Purine metabolism pae00230

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-114i-9732000000-7a823a35c9828d22327c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-9300000000-2f206fd034f1fb2795fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmr-9400000000-a855d87bf0ed7c457172	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w2c-6903000000-621c45a21326a0c06add	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-0415faa4289f87539ce2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-73ad9c3af703650a3eed	View 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

Links

External Links:

Resource	Link
CHEBI ID	18413
HMDB ID	HMDB00999
Pubchem Compound ID	154
Kegg ID	C04640
ChemSpider ID	7830994
Wikipedia ID	Not Available
BioCyc ID	5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
EcoCyc ID	5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE

Phosphoribosylformylglycineamidine (PAMDB000220)

Structure for Phosphoribosylformylglycineamidine (PAMDB000220)