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Record Information
Version	2.0
Creation Date	2012-07-30 14:54:47 -0600
Update Date	2015-06-03 17:20:49 -0600
Secondary Accession Numbers	ECMDB21178
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8a979548> Close
Synonyms:	5-Carboxyamino-1-(5-phospho-D-ribosyl)-imidazole 5-phosphoribosyl-5-carboxyaminoimidazole N5-CAIR N5-CAIR
Chemical Formula:	C9H11N3O9P
Weight:	Average: 336.1721 Monoisotopic: 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
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	Imidazole ribonucleosides and ribonucleotides Glycosylamines Monosaccharide phosphates N-substituted imidazoles Alkyl phosphates Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Organic carbonic acids and derivatives Carbamic acids 1,2-diols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Pentose-5-phosphate Pentose phosphate Imidazole ribonucleoside N-glycosyl compound Glycosyl compound Monosaccharide phosphate Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative N-substituted imidazole Heteroaromatic compound Tetrahydrofuran Imidazole Azole Secondary alcohol Carbonic acid derivative Carbamic acid derivative Carbamic acid 1,2-diol Oxacycle Azacycle Organoheterocyclic compound Organic nitrogen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organonitrogen compound Carbonyl group 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 g/L 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 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 76.05 m³·mol⁻¹ ChemAxon Polarizability 27.05 ų 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 5-Phosphoribosyl-5-carboxyaminoimidazole > 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
SMPDB Pathways:	purine nucleotides de novo biosynthesis 2 PW002033
KEGG Pathways:	Not Available
EcoCyc Pathways:	inosine-5'-phosphate biosynthesis I PWY-6123
Concentrations
	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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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

Enzymes