Record Information |
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Version | 2.0 |
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Created at | 2022-05-12 15:21:52 UTC |
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Updated at | 2022-05-12 15:21:52 UTC |
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NP-MRD ID | NP0136724 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | gamma-Glutamylhistidine |
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Description | Gamma-Glutamylhistidine, also known as L-gamma-glu-L-his or ge-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. Gamma-Glutamylhistidine is a dipeptide composed of gamma-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. Gamma-Glutamylhistidine is a very strong basic compound (based on its pKa). Gamma-Glutamylhistidine is an incomplete breakdown product of protein digestion or protein catabolism. gamma-Glutamylhistidine is found in Lentinula edodes. gamma-Glutamylhistidine was first documented in 1976 (PMID: 932730). These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
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Structure | N[C@@H](CCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O)C(O)=O InChI=1S/C11H16N4O5/c12-7(10(17)18)1-2-9(16)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t7-,8-/m0/s1 |
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Synonyms | Value | Source |
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L-gamma-Glu-L-his | ChEBI | L-g-Glu-L-his | Generator | L-Γ-glu-L-his | Generator | g-Glutamylhistidine | Generator | Γ-glutamylhistidine | Generator | gamma-Glutamate histidine dipeptide | HMDB | gamma-Glutamate-histidine dipeptide | HMDB | GE-H dipeptide | HMDB | GEH dipeptide | HMDB | GGlu-his | HMDB | L-gamma-Glutamyl-L-histidine | HMDB | Γ-glu-his | HMDB | Γ-L-glu-L-his | HMDB | Γ-L-glutamyl-L-histidine | HMDB | L-Γ-glutamyl-L-histidine | HMDB | N-Γ-glutamylhistidine | HMDB | N-L-Γ-glutamylhistidine | HMDB | N-L-Γ-glutamyl-L-histidine | HMDB | gamma-Glu-his | HMDB | gamma-L-Glu-L-his | HMDB | gamma-L-Glutamyl-L-histidine | HMDB | N-gamma-Glutamylhistidine | HMDB | N-L-gamma-Glutamylhistidine | HMDB | N-L-gamma-Glutamyl-L-histidine | HMDB | N-Γ-L-glutamyl-L-histidine | HMDB | N-gamma-L-Glutamyl-L-histidine | HMDB | gamma-Glutamylhistidine | HMDB, ChEBI | g-Glu-his | 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 | (2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid |
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Traditional Name | (2S)-2-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)N[C@@H](CC1=CNC=N1)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C11H16N4O5/c12-7(10(17)18)1-2-9(16)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t7-,8-/m0/s1 |
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InChI Key | PXVCMZCJAUJLJP-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 | |
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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
- Gamma-glutamyl alpha-amino acid
- Histidine or derivatives
- Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-l-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Imidazolyl carboxylic acid derivative
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Heteroaromatic compound
- Azole
- Imidazole
- Amino acid or derivatives
- Secondary carboxylic acid amide
- Carboxamide group
- Amino acid
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid
- Primary amine
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Primary aliphatic amine
- Carbonyl group
- Amine
- Hydrocarbon derivative
- 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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