Fructoselysine (ECMDB20557) (M2MDB001362)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)Transporters (6)XML
Proteins (20)
Record Information
Version2.0
Creation Date2012-05-31 14:50:31 -0600
Update Date2015-06-07 12:23:21 -0600
Secondary Accession Numbers
  • ECMDB20557
Identification
Name:Fructoselysine
DescriptionFructoselysine 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 is invovled in Fructoselysine degradation. Escherichia coli was found to grow on fructoselysine as an energetic substrate at a rate of about one-third of that observed with glucose. (PMID:12147680)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • Fructoselysine
  • Psicoselysine
Chemical Formula:C12H22N2O7
Weight:Average: 306.3123
Monoisotopic: 306.142701068
InChI Key:ZRMPOBPOYIGDMF-UHFFFAOYSA-N
InChI:InChI=1S/C12H22N2O7/c13-6(12(19)20)3-1-2-4-14-11-10(18)9(17)8(16)7(5-15)21-11/h6-9,11,14-17H,1-5,13H2,(H,19,20)
CAS number:Not Available
IUPAC Name:2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid
Traditional IUPAC Name:2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid
SMILES:NC(CCCCNC1OC(CO)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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Oxane
  • Fatty acid
  • Fatty acyl
  • Ketone
  • Cyclic ketone
  • Amino acid
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Alcohol
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility67.3 g/LALOGPS
logP-2.8ALOGPS
logP-4.5ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.34 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.57 m³·mol⁻¹ChemAxon
Polarizability31.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate + Hydrogen ion
Fructoselysine <> Fructoselysine
Fructoselysine <> Fructoselysine
Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate
Fructoselysine <> 1-[(5-Amino-5-carboxypentyl)amino]-1-deoxyfructose
SMPDB Pathways:
Fructoselysine and Psicoselysine DegradationPW002049 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • fructoselysine and psicoselysine degradation PWY0-521
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_55) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08g4-1492000000-4787bf1070b0d9015d20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-4940000000-b1b9e7534d1c743a8fa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9610000000-9289451e9ffaf8102f66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-0934000000-92fe493cacc808bdce6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4s-1930000000-6e8c2c673414bdb6d4fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059b-8900000000-96242a6e67a2a6a514b6View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
  • 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID720
Kegg IDC16488
ChemSpider ID700
Wikipedia IDFructoselysine
BioCyc IDFRUCTOSELYSINE
EcoCyc IDFRUCTOSELYSINE

Enzymes

Protein Details
1. Fructoselysine kinase
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Phosphorylates fructoselysine to yield fructoselysine 6- phosphate
Gene Name:
frlD
Uniprot ID:
P45543
Molecular weight:
28332
Reactions
ATP + fructoselysine = ADP + fructoselysine 6-phosphate.

Transporters

Protein Details
1. Putative fructoselysine transporter frlA
General function:
Involved in amino acid transmembrane transporter activity
Specific function:
May be involved in fructoselysine transport
Gene Name:
frlA
Uniprot ID:
P45539
Molecular weight:
47576
Protein Details
2. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
3. Protein frlC
General function:
Carbohydrate transport and metabolism
Specific function:
Not clear, may be involved in an isomerization step
Gene Name:
frlC
Uniprot ID:
P45541
Molecular weight:
31169
Protein Details
4. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
5. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
6. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368