Record Information |
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Version | 2.0 |
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Created at | 2022-05-12 15:14:45 UTC |
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Updated at | 2022-05-12 15:14:45 UTC |
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NP-MRD ID | NP0136446 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Glutamylhistidine |
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Description | Glutamylhistidine, also known as glu-his or e-H dipeptide, 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. Glutamylhistidine is a dipeptide composed of glutamate and histidine, and is a proteolytic breakdown product of larger proteins. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. Glutamylhistidine is a very strong basic compound (based on its pKa). These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylhistidine was first documented in 1976 (PMID: 932730). Glutamylhistidine is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 7911284). |
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Structure | N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O InChI=1S/C11H16N4O5/c12-7(1-2-9(16)17)10(18)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,18)(H,16,17)(H,19,20)/t7-,8-/m0/s1 |
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Synonyms | Value | Source |
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e-H Dipeptide | HMDB | EH dipeptide | HMDB | Glu-his | HMDB | Glutamate histidine dipeptide | HMDB | Glutamate-histidine dipeptide | HMDB | L-Glutamyl-L-histidine | HMDB | Α-glu-his | HMDB | Α-L-glu-L-his | HMDB | Α-glutamylhistidine | HMDB | Α-L-glutamyl-L-histidine | HMDB | L-Α-glutamyl-L-histidine | HMDB | N-Α-glutamylhistidine | HMDB | N-Α-L-glutamyl-L-histidine | HMDB | N-L-Α-glutamylhistidine | HMDB | N-L-Α-glutamyl-L-histidine | HMDB | alpha-Glu-his | HMDB | alpha-L-Glu-L-his | HMDB | alpha-Glutamylhistidine | HMDB | alpha-L-Glutamyl-L-histidine | HMDB | L-alpha-Glutamyl-L-histidine | HMDB | N-alpha-Glutamylhistidine | HMDB | N-alpha-L-Glutamyl-L-histidine | HMDB | N-L-alpha-Glutamylhistidine | HMDB | N-L-alpha-Glutamyl-L-histidine | HMDB | L-Glu-L-his | HMDB | N-Glutamylhistidine | HMDB | N-L-Glutamyl-L-histidine | HMDB | Glutamyl-histidine | HMDB | Glutamic acid histidine dipeptide | HMDB | Glutamic acid-histidine dipeptide | HMDB | Glutamylhistidine | HMDB | (4S)-4-Amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}butanoate | Generator |
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Chemical Formula | C11H16N4O5 |
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Average Mass | 284.2720 Da |
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Monoisotopic Mass | 284.11207 Da |
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IUPAC Name | (4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid |
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Traditional Name | (4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid |
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CAS Registry Number | Not Available |
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SMILES | N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O |
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InChI Identifier | InChI=1S/C11H16N4O5/c12-7(1-2-9(16)17)10(18)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,18)(H,16,17)(H,19,20)/t7-,8-/m0/s1 |
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InChI Key | HKTRDWYCAUTRRL-YUMQZZPRSA-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, 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 |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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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. |
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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 | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Histidine or derivatives
- 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
- Imidazolyl carboxylic acid derivative
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid
- Primary amine
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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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