| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-05-11 16:41:38 UTC |
|---|
| Updated at | 2022-05-11 16:41:38 UTC |
|---|
| NP-MRD ID | NP0087153 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | L-alpha-Glutamyl-L-lysine |
|---|
| Description | Glutamyllysine, also known as L-glu-L-lys or E-K, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. L-alpha-Glutamyl-L-lysine was first documented in 2002 (PMID: 12351458). Glutamyllysine is a very strong basic compound (based on its pKa) (PMID: 15746190). |
|---|
| Structure | NCCCC[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O InChI=1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-10(17)7(13)4-5-9(15)16/h7-8H,1-6,12-13H2,(H,14,17)(H,15,16)(H,18,19)/t7-,8-/m0/s1 |
|---|
| Synonyms | | Value | Source |
|---|
| E-K | ChEBI | | EK | ChEBI | | L-Glu-L-lys | ChEBI | | N2-a-Glutamyl-lysine | HMDB | | N2-alpha-Glutamyl-lysine | HMDB | | N2-L-a-Glutamyl-lysine | HMDB | | N2-L-a-Glutamyllysine | HMDB | | N2-L-alpha-Glutamyllysine | HMDB | | Α-glu-lys | HMDB | | Α-L-glu-L-lys | HMDB | | Α-glutamyllysine | HMDB | | Α-L-glutamyl-L-lysine | HMDB | | L-Α-glutamyl-L-lysine | HMDB | | N2-Α-glutamyllysine | HMDB | | N2-Α-L-glutamyl-L-lysine | HMDB | | N2-L-Α-glutamyllysine | HMDB | | N2-L-Α-glutamyl-L-lysine | HMDB | | alpha-Glu-lys | HMDB | | alpha-L-Glu-L-lys | HMDB | | alpha-Glutamyllysine | HMDB | | alpha-L-Glutamyl-L-lysine | HMDB | | L-alpha-Glutamyl-L-lysine | HMDB | | N2-alpha-Glutamyllysine | HMDB | | N2-alpha-L-Glutamyl-L-lysine | HMDB | | N2-L-alpha-Glutamyl-L-lysine | HMDB | | Glu-lys | HMDB | | L-Glutamyl-L-lysine | HMDB | | N2-Glutamyllysine | HMDB | | N2-L-Glutamyl-L-lysine | HMDB | | Glutamyl-lysine | HMDB | | Glutamic acid lysine dipeptide | HMDB | | Glutamate lysine dipeptide | HMDB | | Glutamic acid-lysine dipeptide | HMDB | | Glutamate-lysine dipeptide | HMDB | | e-K Dipeptide | HMDB | | EK dipeptide | HMDB | | N2-L-alpha-Glutamyl-lysine | HMDB | | L-a-Glutamyl-L-lysine | HMDB | | Glutamyllysine | HMDB |
|
|---|
| Chemical Formula | C11H21N3O5 |
|---|
| Average Mass | 275.3015 Da |
|---|
| Monoisotopic Mass | 275.14812 Da |
|---|
| IUPAC Name | (2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoic acid |
|---|
| Traditional Name | L-α-glutamyl-L-lysine |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | NCCCC[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O |
|---|
| InChI Identifier | InChI=1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-10(17)7(13)4-5-9(15)16/h7-8H,1-6,12-13H2,(H,14,17)(H,15,16)(H,18,19)/t7-,8-/m0/s1 |
|---|
| InChI Key | BBBXWRGITSUJPB-YUMQZZPRSA-N |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | Dipeptides |
|---|
| Alternative Parents | |
|---|
| Substituents | - Alpha-dipeptide
- Glutamic acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Medium-chain fatty acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Fatty acid
- Amino acid or derivatives
- Carboxamide group
- Carboxylic acid salt
- Amino acid
- Secondary carboxylic acid amide
- Carboxylic acid
- Organic salt
- Hydrocarbon derivative
- Primary aliphatic amine
- Amine
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Organic zwitterion
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| General References | - van Rossum EF, Koper JW, Huizenga NA, Uitterlinden AG, Janssen JA, Brinkmann AO, Grobbee DE, de Jong FH, van Duyn CM, Pols HA, Lamberts SW: A polymorphism in the glucocorticoid receptor gene, which decreases sensitivity to glucocorticoids in vivo, is associated with low insulin and cholesterol levels. Diabetes. 2002 Oct;51(10):3128-34. doi: 10.2337/diabetes.51.10.3128. [PubMed:12351458 ]
- Russcher H, van Rossum EF, de Jong FH, Brinkmann AO, Lamberts SW, Koper JW: Increased expression of the glucocorticoid receptor-A translational isoform as a result of the ER22/23EK polymorphism. Mol Endocrinol. 2005 Jul;19(7):1687-96. doi: 10.1210/me.2004-0467. Epub 2005 Mar 3. [PubMed:15746190 ]
|
|---|