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Record Information
Version	2.0
Creation Date	2012-05-31 14:50:34 -0600
Update Date	2015-06-03 17:20:18 -0600
Secondary Accession Numbers	ECMDB20558
Identification
Name:	Fructoselysine-6-phosphate
Description	Fructoselysine-6-phosphate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Fructoselysine-6-phosphate is invovled in Fructoselysine degradation. Fructoselysine-6-phosphate is involved in the metabolism of fructation product. The metabolism of the glycation product fructose-epsilon-lysine in Escherichia coli involves its ATP-dependent phosphorylation by a specific kinase (FrlD), followed by the conversion of fructoselysine 6-phosphate into glucose 6-phosphate and lysine by fructoselysine-6-phosphate deglycase (FrlB), which is distantly related to the isomerase domain of glucosamine-6-phosphate synthase. (PMID 16153181)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa0ec2958> Close
Synonyms:	Fructoselysine 6-phosphate Fructoselysine 6-phosphoric acid Fructoselysine-6-P Fructoselysine-6-phosphoric acid
Chemical Formula:	C12H23N2O10P
Weight:	Average: 386.2922 Monoisotopic: 386.109031478
InChI Key:	BZFCRRVQZCIOBA-UHFFFAOYSA-N
InChI:	InChI=1S/C12H23N2O10P/c13-6(12(18)19)3-1-2-4-14-11-10(17)9(16)8(15)7(24-11)5-23-25(20,21)22/h6-9,11,14-16H,1-5,13H2,(H,18,19)(H2,20,21,22)
CAS number:	Not Available
IUPAC Name:	2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid
Traditional IUPAC Name:	2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid
SMILES:	NC(CCCCNC1OC(COP(O)(O)=O)C(O)C(O)C1=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Alpha amino acids
Alternative Parents	Medium-chain fatty acids Hydroxy fatty acids Monoalkyl phosphates Oxanes Monosaccharides Secondary alcohols 1,2-diols Amino acids Cyclic ketones Oxacyclic compounds Carboxylic acids Dialkylamines Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Organic oxides Monoalkylamines
Substituents	Alpha-amino acid Medium-chain fatty acid Hydroxy fatty acid Monoalkyl phosphate Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Alkyl phosphate Fatty acid Fatty acyl Amino acid Cyclic ketone Ketone 1,2-diol Secondary alcohol Secondary amine Organoheterocyclic compound Secondary aliphatic amine Oxacycle Monocarboxylic acid or derivatives Carboxylic acid Organic oxide Alcohol Organonitrogen compound Primary aliphatic amine Organooxygen compound Organic oxygen compound Hydrocarbon derivative Organic nitrogen compound Carbonyl group Primary amine Organopnictogen compound Amine Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.16 g/L ALOGPS logP -2.1 ALOGPS logP -8.2 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.07 ChemAxon pKa (Strongest Basic) 9.32 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 208.87 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 80.45 m³·mol⁻¹ ChemAxon Polarizability 35.8 ų ChemAxon Number of Rings 1 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:	Fructoselysine-6-phosphate + Water <> Glucose 6-phosphate + L-Lysine Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate + Hydrogen ion Fructoselysine-6-phosphate + Water > Glucose 6-phosphate + L-Lysine Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate 1-[(5-Amino-5-carboxypentyl)amino]-1-deoxyfructose + Adenosine triphosphate > Fructoselysine-6-phosphate + ADP + Hydrogen ion Fructoselysine-6-phosphate + Water <> β-D-glucose 6-phosphate + L-Lysine
SMPDB Pathways:	Fructoselysine and Psicoselysine Degradation PW002049
KEGG Pathways:	Not Available
EcoCyc Pathways:	fructoselysine and psicoselysine degradation PWY0-521
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_82) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00ku-1329000000-45bc525596d4fe9c5a69 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0f7n-5923000000-f3fd3f8e42b8567c1eb6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001j-7920000000-dab81d34a57b60e30437 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-5916000000-0f9797f9fc948edd0c14 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9510000000-b68cbc30b57ea1b0f23e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-9ee8e58b2ff830436867 View in MoNA MS Mass Spectrum (Electron Ionization) 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 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 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 Wiame, E., Lamosa, P., Santos, H., Van Schaftingen, E. (2005). "Identification of glucoselysine-6-phosphate deglycase, an enzyme involved in the metabolism of the fructation product glucoselysine." Biochem J 392:263-269. Pubmed: 16153181 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 Not Available HMDB ID Not Available Pubchem Compound ID 721 Kegg ID Not Available ChemSpider ID 701 Wikipedia ID Not Available BioCyc ID FRUCTOSELYSINE-6-PHOSPHATE EcoCyc ID FRUCTOSELYSINE-6-PHOSPHATE

Enzymes