| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 01:00:00 UTC |
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| Updated at | 2022-09-02 01:00:01 UTC |
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| NP-MRD ID | NP0145745 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | fructoselysine |
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| Description | Fructosyllysine 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). |
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| Structure | N[C@@H](CCCCNCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO)C(O)=O 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 |
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| Synonyms | | Value | Source |
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| 1-{[(5S)-5-amino-5-carboxypentyl]amino}-1-deoxy-D-fructose | ChEBI | | epsilon-Fructoselysine | ChEBI | | epsilon-Fructosyl-L-lysine | ChEBI | | Fructose lysine | ChEBI | | Fructosyl-lysine | ChEBI | | Fructoselysine | MeSH |
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| Chemical Formula | C12H24N2O7 |
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| Average Mass | 308.3310 Da |
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| Monoisotopic Mass | 308.15835 Da |
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| IUPAC Name | (2S)-2-amino-6-{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino}hexanoic acid |
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| Traditional Name | fructosyl-lysine |
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| CAS Registry Number | Not Available |
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| SMILES | N[C@@H](CCCCNCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO)C(O)=O |
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| 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 |
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| InChI Key | BFSYFTQDGRDJNV-AYHFEMFVSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | L-alpha-amino acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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