| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-12 15:14:28 UTC |
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| Updated at | 2022-05-12 15:14:28 UTC |
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| NP-MRD ID | NP0136435 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Glutaminyltryptophan |
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| Description | Glutaminyltryptophan, also known as Q-W dipeptide or L-GLN-L-TRP, 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. Glutaminyltryptophan is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. |
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| Structure | N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O InChI=1S/C16H20N4O4/c17-11(5-6-14(18)21)15(22)20-13(16(23)24)7-9-8-19-12-4-2-1-3-10(9)12/h1-4,8,11,13,19H,5-7,17H2,(H2,18,21)(H,20,22)(H,23,24)/t11-,13-/m0/s1 |
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| Synonyms | | Value | Source |
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| (2S)-2-{[(2S)-2,5-diamino-5-oxopentanoyl]amino}-3-(1H-indol-3-yl)propanoic acid | ChEBI | | Glutamine tryptophan dipeptide | ChEBI | | Glutamine-tryptophan | ChEBI | | L-GLN-L-TRP | ChEBI | | N-Glutaminyltryptophan | ChEBI | | N-L-Glutaminyl-L-tryptophan | ChEBI | | Q-W | ChEBI | | Q-W Dipeptide | ChEBI | | QW | ChEBI | | QW Dipeptide | ChEBI | | (2S)-2-{[(2S)-2,5-diamino-5-oxopentanoyl]amino}-3-(1H-indol-3-yl)propanoate | Generator | | GLN-TRP | HMDB | | L-Glutaminyl-L-tryptophan | HMDB | | Glutaminyl-tryptophan | HMDB | | Glutamine-tryptophan dipeptide | HMDB | | Glutaminyltryptophan | HMDB, ChEBI | | (2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-(1H-indol-3-yl)propanoate | Generator |
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| Chemical Formula | C16H20N4O4 |
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| Average Mass | 332.3600 Da |
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| Monoisotopic Mass | 332.14846 Da |
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| IUPAC Name | (2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(1H-indol-3-yl)propanoic acid |
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| Traditional Name | (2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(1H-indol-3-yl)propanoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O |
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| InChI Identifier | InChI=1S/C16H20N4O4/c17-11(5-6-14(18)21)15(22)20-13(16(23)24)7-9-8-19-12-4-2-1-3-10(9)12/h1-4,8,11,13,19H,5-7,17H2,(H2,18,21)(H,20,22)(H,23,24)/t11-,13-/m0/s1 |
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| InChI Key | ZQFAGNFSIZZYBA-AAEUAGOBSA-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
- Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- Indolyl carboxylic acid derivative
- Alpha-amino acid or derivatives
- 3-alkylindole
- Indole
- Indole or derivatives
- Fatty amide
- Fatty acyl
- Benzenoid
- Substituted pyrrole
- N-acyl-amine
- Pyrrole
- Heteroaromatic compound
- Primary carboxylic acid amide
- Secondary carboxylic acid amide
- Carboxamide group
- Amino acid
- Amino acid or derivatives
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Primary amine
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Primary aliphatic amine
- Organic oxide
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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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