P. aeruginosa Metabolome Database: 5-Phosphoribosyl-5-carboxyaminoimidazole (PAMDB001587)

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

PAMDB001587

Identification

Name:

5-Phosphoribosyl-5-carboxyaminoimidazole

Description:

5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole is an intermediate in purine metabolism and IMP biosynthesis via the de novo pathway. It is a substrate of the PurK enzyme which catalyzes the ATP-dependent conversion of 5-aminoimidazole ribonucleotide (AIR) and HCO3- to N5-carboxyaminoimidazole ribonucleotide (N5-CAIR).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5-Carboxyamino-1-(5-phospho-D-ribosyl)-imidazole
5-phosphoribosyl-5-carboxyaminoimidazole
N⁵-CAIR
N5-CAIR

Chemical Formula:

C₉H₁₁N₃O₉P

Average Molecular Weight:

336.1721

Monoisotopic Molecular Weight:

336.023290477

InChI Key:

JHLXDWGVSYMXPL-UHFFFAOYSA-K

InChI:

InChI=1S/C9H14N3O9P/c13-6-4(2-20-22(17,18)19)21-8(7(6)14)12-3-10-1-5(12)11-9(15)16/h1,3-4,6-8,11,13-14H,2H2,(H,15,16)(H2,17,18,19)/p-3

CAS number:

Not Available

IUPAC Name:

N-(1-{3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)carbamate

Traditional IUPAC Name:

N-(3-{3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl}imidazol-4-yl)carbamate

SMILES:

OC1C(O)C(OC1COP([O-])([O-])=O)N1C=NC=C1NC([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazoles. These are organic compounds containing the imidazole ring 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-phosphoribosyl-imidazoles

Direct Parent

1-phosphoribosyl-imidazoles

Alternative Parents

Substituents

1-phosphoribosyl-imidazole
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Aminoimidazole
Heteroaromatic compound
Oxolane
Imidazole
Azole
Secondary alcohol
Carbamic acid derivative
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD0-181 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.52 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	5.83	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	192.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.05 m³·mol^-1	ChemAxon
Polarizability	27.05 Å³	ChemAxon
Number of Rings	2	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:

5-Aminoimidazole ribonucleotide + Adenosine triphosphate + Hydrogen carbonate > 5-Phosphoribosyl-5-carboxyaminoimidazole + ADP + Hydrogen ion + Phosphate
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Phosphoribosyl-5-carboxyaminoimidazole

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-59a258785315de737eb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0119000000-3c24b671f00e253952c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000y-7920000000-71a059951733c823f7e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-357eaf776f2045653354	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-3119000000-a5ab9eda349cf23bb092	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003s-9000000000-648a69b10d5145733551	View in MoNA

References

References:

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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	25244287
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-181
EcoCyc ID	CPD0-181

5-Phosphoribosyl-5-carboxyaminoimidazole (PAMDB001587)

Structure for 5-Phosphoribosyl-5-carboxyaminoimidazole (PAMDB001587)