Np mrd loader

Record Information
Version2.0
Created at2022-09-02 01:00:00 UTC
Updated at2022-09-02 01:00:01 UTC
NP-MRD IDNP0145745
Secondary Accession NumbersNone
Natural Product Identification
Common Namefructoselysine
DescriptionFructosyllysine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Fructosyllysine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. fructoselysine is found in Trypanosoma brucei. fructoselysine was first documented in 2020 (PMID: 33205653). Based on a literature review a small amount of articles have been published on fructosyllysine (PMID: 35885358) (PMID: 34556332) (PMID: 33992388) (PMID: 33348132).
Structure
Thumb
Synonyms
ValueSource
1-{[(5S)-5-amino-5-carboxypentyl]amino}-1-deoxy-D-fructoseChEBI
epsilon-FructoselysineChEBI
epsilon-Fructosyl-L-lysineChEBI
Fructose lysineChEBI
Fructosyl-lysineChEBI
FructoselysineMeSH
Chemical FormulaC12H24N2O7
Average Mass308.3310 Da
Monoisotopic Mass308.15835 Da
IUPAC Name(2S)-2-amino-6-{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino}hexanoic acid
Traditional Namefructosyl-lysine
CAS Registry NumberNot Available
SMILES
N[C@@H](CCCCNCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO)C(O)=O
InChI Identifier
InChI=1S/C12H24N2O7/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21)/t7-,9+,10+,11+/m0/s1
InChI KeyBFSYFTQDGRDJNV-AYHFEMFVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Hydroxy fatty acid
  • Acyloin
  • Beta-hydroxy ketone
  • Monosaccharide
  • Fatty acid
  • Fatty acyl
  • Alpha-aminoketone
  • Alpha-hydroxy ketone
  • 1,3-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Ketone
  • Secondary amine
  • Polyol
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
logP-5.5ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.34 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity71.88 m³·mol⁻¹ChemAxon
Polarizability31.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8015298
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFructoselysine
METLIN IDNot Available
PubChem Compound9839580
PDB IDNot Available
ChEBI ID24109
Good Scents IDNot Available
References
General References
  1. Manig F, Hellwig M, Pietz F, Henle T: Studies about the Dietary Impact on "Free" Glycation Compounds in Human Saliva. Foods. 2022 Jul 15;11(14):2112. doi: 10.3390/foods11142112. [PubMed:35885358 ]
  2. Lind L: The metabolomic profile of carotid artery intima-media thickness and echogenicity. Atherosclerosis. 2021 Oct;335:142-147. doi: 10.1016/j.atherosclerosis.2021.09.011. Epub 2021 Sep 13. [PubMed:34556332 ]
  3. Zhao X, Zhang X, Ye B, Yan H, Zhao Y, Liu L: Effect of unsaturated fatty acids on glycation product formation pathways. Food Res Int. 2021 May;143:110288. doi: 10.1016/j.foodres.2021.110288. Epub 2021 Mar 8. [PubMed:33992388 ]
  4. Zhang H, Troise AD, Zhang H, Fogliano V: Cocoa melanoidins reduce the formation of dietary advanced glycation end-products in dairy mimicking system. Food Chem. 2021 May 30;345:128827. doi: 10.1016/j.foodchem.2020.128827. Epub 2020 Dec 8. [PubMed:33348132 ]
  5. Hellwig M, Henle T: Maillard Reaction Products in Different Types of Brewing Malt. J Agric Food Chem. 2020 Nov 18. doi: 10.1021/acs.jafc.0c06193. [PubMed:33205653 ]
  6. LOTUS database [Link]