P. aeruginosa Metabolome Database: Phosphoribulosylformimino-AICAR-P (PAMDB000838)

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

PAMDB000838

Identification

Name:

Phosphoribulosylformimino-AICAR-P

Description:

Phosphoribulosylformimino-aicar-p is a member of the chemical class known as 1-Phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond. PRFAR is catalyzed by imidazole glycerol phosphate syntahse. Imidazole glycerol phosphate (IGP) synthase is a glutamine amidotransferase that catalyzes the formation of IGP and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) from N(1)-[(5'-phosphoribulosyl)formimino]-5-aminoimidazole-4-car boxamide ribonucleotide (PRFAR). (PMID 10733892). 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide is an intermediate in the histidine biosynthesis pathway. It is a substrate for the enzyme 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase which catalyzes the reaction 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5-[(5-Phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide
N-(5'-Phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide
N-(5'Phospho-D-1'-ribulosylformimino)-5-amino-1-(5-phosphoribosyl)-4-imidazolecarboxamide
Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphate
Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphoric acid
Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphate
Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphoric acid
Phosphoribulosyl-formimino-aicar-p
Phosphoribulosylformiminoaicar-phosphate
Phosphoribulosylformiminoaicar-phosphoric acid
Prfar
PRuFAP

Chemical Formula:

C₁₅H₂₅N₅O₁₅P₂

Average Molecular Weight:

577.331

Monoisotopic Molecular Weight:

577.082238179

InChI Key:

BLKFNHOCHNCLII-IIZOACFYSA-N

InChI:

InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/t7-,8+,10+,11+,12+,15+/m1/s1

CAS number:

Not Available

IUPAC Name:

{[(2R,3R)-5-[(E)-N'-{4-carbamoyl-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid

Traditional IUPAC Name:

[(2R,3R)-5-[(E)-N'-{5-carbamoyl-3-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxyphosphonic acid

SMILES:

O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-phosphoribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-phosphoribosyl-imidazolecarboxamide
1-phosphoribosyl-imidazole
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Saccharide
Beta-hydroxy ketone
Beta-ketoaldehyde
Aminoimidazole
Acyloin
Heteroaromatic compound
Vinylogous amide
Oxolane
Imidazole
Azole
Alpha-hydroxy ketone
Alpha-aminoketone
Secondary alcohol
Primary carboxylic acid amide
Ketone
Carboxamide group
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboxylic acid amidine
Amidine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.21 mg/mL	ALOGPS
logP	-2	ALOGPS
logP	-5.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	7.35	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	326.04 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	116.21 m³·mol^-1	ChemAxon
Polarizability	48.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	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:

L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion
Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate
PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P
Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR
Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate

Pathways:

Histidine metabolism pae00340
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0129250000-34da0f09334273bb5733	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1749000000-35b2fd0c7ba2bf365cc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1953000000-905c7e021fac249fd064	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-9677450000-0060eff9af2626729618	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9211000000-6721677e2439e38c5466	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b9e22a6bd0b38386b60d	View in MoNA

References

References:

Chittur, S. V., Chen, Y., Davisson, V. J. (2000). "Expression and purification of imidazole glycerol phosphate synthase from Saccharomyces cerevisiae." Protein Expr Purif 18:366-377. Pubmed: 10733892
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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB12278
Pubchem Compound ID	1013
Kegg ID	C04916
ChemSpider ID	30776607
Wikipedia ID	Not Available
BioCyc ID	PHOSPHORIBULOSYL-FORMIMINO-AICAR-P
EcoCyc ID	PHOSPHORIBULOSYL-FORMIMINO-AICAR-P

Phosphoribulosylformimino-AICAR-P (PAMDB000838)

Structure for Phosphoribulosylformimino-AICAR-P (PAMDB000838)