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Record Information
Version	2.0
Creation Date	2012-05-31 13:45:51 -0600
Update Date	2015-09-17 15:41:09 -0600
Secondary Accession Numbers	ECMDB01128
Identification
Name:	5-Phosphoribosylamine
Description	5-Phosphoribosylamine is a substrate for Amidophosphoribosyltransferase and Trifunctional purine biosynthetic protein adenosine-3.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae89c4f8> Close
Synonyms:	5-P-β-D-ribosyl-amine 5-P-b-D-Ribosyl-amine 5-P-b-delta-Ribosyl-amine 5-P-b-δ-Ribosyl-amine 5-P-beta-D-Ribosyl-amine 5-P-beta-delta-Ribosyl-amine 5-P-β-D-Ribosyl-amine 5-P-β-δ-Ribosyl-amine 5-phospho-b-D-Ribosyl-amine 5-phospho-b-D-Ribosylamine 5-phospho-b-delta-Ribosyl-amine 5-phospho-b-delta-Ribosylamine 5-phospho-b-δ-Ribosyl-amine 5-phospho-b-δ-Ribosylamine 5-Phospho-beta-D-ribosyl-amine 5-Phospho-beta-D-ribosylamine 5-Phospho-beta-delta-ribosyl-amine 5-Phospho-beta-delta-ribosylamine 5-Phospho-D-ribosylamine 5-Phospho-delta-ribosylamine 5-phospho-β-D-Ribosyl-amine 5-phospho-β-D-Ribosylamine 5-phospho-β-δ-Ribosyl-amine 5-phospho-β-δ-Ribosylamine 5-phospho-δ-Ribosylamine 5-Phosphoribosylamine PRA
Chemical Formula:	C5H12NO7P
Weight:	Average: 229.125 Monoisotopic: 229.035138255
InChI Key:	SKCBPEVYGOQGJN-TXICZTDVSA-N
InChI:	InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
CAS number:	Not Available
IUPAC Name:	{[(2R,3S,4R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:	5-phospho-D-ribosylamine
SMILES:	N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
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	Monosaccharide phosphates Monoalkyl phosphates Tetrahydrofurans Secondary alcohols Hemiaminals 1,2-diols Oxacyclic compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
Substituents	Pentose phosphate Pentose-5-phosphate Monosaccharide phosphate Monoalkyl phosphate Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Tetrahydrofuran Secondary alcohol 1,2-diol Hemiaminal Organoheterocyclic compound Oxacycle Alcohol Organic oxide Organopnictogen compound Organonitrogen compound Organic nitrogen compound Primary aliphatic amine Hydrocarbon derivative Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	ribose monophosphate (CHEBI:17284 ) ribosylamine (CHEBI:17284 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 38.2 g/L ALOGPS logP -2.4 ALOGPS logP -3.5 ChemAxon logS -0.78 ALOGPS pKa (Strongest Acidic) 1.23 ChemAxon pKa (Strongest Basic) 8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 142.47 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 42.49 m³·mol⁻¹ ChemAxon Polarizability 18.64 ų 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:	L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate + 5-Phosphoribosylamine Adenosine triphosphate + Glycine + 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + Phosphate 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + Water Adenosine triphosphate + 5-Phosphoribosylamine + Glycine <> ADP + Phosphate + Glycineamideribotide 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + Water 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate > L-Glutamine + Phosphoribosyl pyrophosphate + Water Adenosine triphosphate + 5-Phosphoribosylamine + Glycine > ADP + Inorganic phosphate + 5'-Phospho-ribosylglycinamide Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-Glutamate 5-Phosphoribosylamine + Glycine + Adenosine triphosphate + 5-Phosphoribosylamine > N1-(5-phospho-β-D-ribosyl)glycinamide + Phosphate + Adenosine diphosphate + Hydrogen ion + ADP L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine 5 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + Water Adenosine triphosphate + Glycine + 5 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + Phosphate L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine
SMPDB Pathways:	Thiamin diphosphate biosynthesis PW002028 purine nucleotides de novo biosynthesis PW000910 purine nucleotides de novo biosynthesis 1435709748 PW000960 purine nucleotides de novo biosynthesis 2 PW002033
KEGG Pathways:	Alanine, aspartate and glutamate metabolism ec00250 Metabolic pathways eco01100 Purine metabolism ec00230
EcoCyc Pathways:	5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122 superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-2590000000-701d3e4cccc695f0ec9f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01q9-8940000000-72b65d39cdc2ac61ecf7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0007-9100000000-a5c27bfd695bb49e9570 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9040000000-c9c5fb67cd4a6a7824db View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-a36fea1c5e53487160b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-554f2cc279bae943d47d View in MoNA
References
References:	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 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 17284 HMDB ID HMDB01128 Pubchem Compound ID 150 Kegg ID C03090 ChemSpider ID 388939 Wikipedia 5-phosphoribosylamine BioCyc ID 5-P-BETA-D-RIBOSYL-AMINE EcoCyc ID 5-P-BETA-D-RIBOSYL-AMINE

Enzymes