Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:42 UTC |
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Update date | 2020-09-17 15:38:24 UTC |
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Primary ID | FDB000787 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Asparagine |
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Description | L-Asparagine, also known as Asn or aspartamic acid, belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Asparagine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Asparagine is a very strong basic compound (based on its pKa). L-Asparagine exists in all living species, ranging from bacteria to humans. Within humans, L-asparagine participates in a number of enzymatic reactions. In particular, L-asparagine and L-glutamic acid can be biosynthesized from L-aspartic acid and L-glutamine through the action of the enzyme asparagine synthetase [glutamine-hydrolyzing]. In addition, L-asparagine can be converted into L-aspartic acid through the action of the enzyme isoaspartyl peptidase/l-asparaginase. In humans, L-asparagine is involved in aspartate metabolism. L-Asparagine is an odorless tasting compound. Outside of the human body, L-Asparagine is found, on average, in the highest concentration within a few different foods, such as white lupines, wheats, and oats and in a lower concentration in sacred lotus, parsnips, and pineapples. L-Asparagine has also been detected, but not quantified in, several different foods, such as colorado pinyons, opium poppies, lentils, green beans, and watermelons. This could make L-asparagine a potential biomarker for the consumption of these foods. L-Asparagine is a potentially toxic compound. An optically active form of asparagine having L-configuration. |
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CAS Number | 70-47-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S)-2,4-Diamino-4-oxobutanoic acid | ChEBI | (2S)-2-Amino-3-carbamoylpropanoic acid | ChEBI | (S)-2-Amino-3-carbamoylpropanoic acid | ChEBI | (S)-Asparagine | ChEBI | 2-Aminosuccinamic acid | ChEBI | alpha-Aminosuccinamic acid | ChEBI | Asn | ChEBI | ASPARAGINE | ChEBI | Aspartamic acid | ChEBI | L-2-Aminosuccinamic acid | ChEBI | L-Asparagin | ChEBI | L-Aspartic acid beta-amide | ChEBI | N | ChEBI | (2S)-2,4-Diamino-4-oxobutanoate | Generator | (2S)-2-Amino-3-carbamoylpropanoate | Generator | (S)-2-Amino-3-carbamoylpropanoate | Generator | 2-Aminosuccinamate | Generator | a-Aminosuccinamate | Generator | a-Aminosuccinamic acid | Generator | alpha-Aminosuccinamate | Generator | Α-aminosuccinamate | Generator | Α-aminosuccinamic acid | Generator | Aspartamate | Generator | L-2-Aminosuccinamate | Generator | L-Aspartate b-amide | Generator | L-Aspartate beta-amide | Generator | L-Aspartate β-amide | Generator | L-Aspartic acid b-amide | Generator | L-Aspartic acid β-amide | Generator | (-)-Asparagine | HMDB | (S)-2,4-Diamino-4-oxobutanoate | HMDB | (S)-2,4-Diamino-4-oxobutanoic acid | HMDB | Agedoite | HMDB | alpha Amminosuccinamate | HMDB | alpha Amminosuccinamic acid | HMDB | Altheine | HMDB | Asparagine acid | HMDB | Asparamide | HMDB | Aspartic acid amide | HMDB | Aspartic acid b-amide | HMDB | Aspartic acid beta amide | HMDB | b2,4-(S)-Diamino-4-oxo-utanoate | HMDB | b2,4-(S)-Diamino-4-oxo-utanoic acid | HMDB | Crystal VI | HMDB | L-2,4-Diamino-4-oxobutanoate | HMDB | L-2,4-Diamino-4-oxobutanoic acid | HMDB | L-Aspartamine | HMDB | L-b-Asparagine | HMDB | L-beta-Asparagine | HMDB | (2S)-2-amino-3-Carbamoylpropanoate | Generator | (S)-2-amino-3-Carbamoylpropanoate | Generator | (S)-2-Aminosuccinic acid 4-amide | biospider | 2-Aminosuccinamic acid, L- | biospider | Asparagine, 9CI; L-form | db_source | Asparagine, L- (8CI) | biospider | L-Asparagine (9CI) | biospider | L-Asparatamine | biospider | L-Aspartic acid 4-amide | biospider | α-aminosuccinamate | Generator | α-aminosuccinamic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C4H8N2O3 |
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IUPAC name | (2S)-2-amino-3-carbamoylpropanoic acid |
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InChI Identifier | InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 |
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InChI Key | DCXYFEDJOCDNAF-REOHCLBHSA-N |
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Isomeric SMILES | N[C@@H](CC(N)=O)C(O)=O |
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Average Molecular Weight | 132.1179 |
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Monoisotopic Molecular Weight | 132.053492132 |
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Classification |
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Description | Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Asparagine and derivatives |
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Alternative Parents | |
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Substituents | - Asparagine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Fatty amide
- Fatty acyl
- Fatty acid
- Carboxamide group
- Amino acid
- Primary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Environmental role: Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 36.36%; H 6.10%; N 21.20%; O 36.33% | DFC |
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Melting Point | Mp 226-227 dec. (slow heat) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 29.4 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -3.82 | CHMELIK,J ET AL. (1991) |
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Experimental pKa | pKa2 8.6 (NH2) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D +33.2 (3M HCl) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | L-Asparagine, 3 TMS, GC-MS Spectrum | splash10-0159-0910000000-bedf57998656ab5ebc16 | Spectrum | GC-MS | L-Asparagine, 3 TMS, GC-MS Spectrum | splash10-0159-0910000000-4979c4d028d2dc931263 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-b7ea3fef61f3940cbdda | Spectrum | GC-MS | L-Asparagine, 3 TMS, GC-MS Spectrum | splash10-00di-9710000000-6d0afcbcc003347e598e | Spectrum | GC-MS | L-Asparagine, 2 TMS, GC-MS Spectrum | splash10-0uxr-0910000000-2be567239bd3229b1ca1 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-02t9-0790000000-b8141f48cbebb90f683e | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-02t9-1790000000-1d12ed9b4fb2799da766 | Spectrum | GC-MS | L-Asparagine, 4 TMS, GC-MS Spectrum | splash10-014u-0961000000-65a5c0999f17110c9939 | Spectrum | GC-MS | L-Asparagine, 4 TMS, GC-MS Spectrum | splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e | Spectrum | GC-MS | L-Asparagine, 3 TMS, GC-MS Spectrum | splash10-00lr-1920000000-7864dbb1f685e64dd1cf | Spectrum | GC-MS | L-Asparagine, 4 TMS, GC-MS Spectrum | splash10-000i-1940000000-964ea25da2789805985a | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-00lr-0930000000-79a089d9875e092dd7f2 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-bedf57998656ab5ebc16 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-4979c4d028d2dc931263 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-b7ea3fef61f3940cbdda | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-00di-4931100000-17f149310ce3a0f748d1 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-00di-9710000000-6d0afcbcc003347e598e | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-0uxr-0910000000-2be567239bd3229b1ca1 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-02t9-0790000000-b8141f48cbebb90f683e | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-02t9-1790000000-1d12ed9b4fb2799da766 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-014u-0961000000-65a5c0999f17110c9939 | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-00lr-1920000000-7864dbb1f685e64dd1cf | Spectrum | GC-MS | L-Asparagine, non-derivatized, GC-MS Spectrum | splash10-000i-1940000000-964ea25da2789805985a | Spectrum | Predicted GC-MS | L-Asparagine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000f-9100000000-5881591331bd059b7e7d | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0080-9400000000-e5c7e19f427eea6d71b0 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-afc1214100db1168b095 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00dl-9000000000-57e977cd87e9a86d482b | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-6fb96f5aa291359dba29 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-76f11e6fe5657c35d15f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-e944486273dbfde4cae4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-27ad91a86be0c4d86c3c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-b8b7a3431b66246ad613 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-03fa294ec740e189dd99 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-cee2081406fc25ab6169 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-cd79afa0c27f65e54adc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-01q9-0943200000-5a24322ba0ce2f410155 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-fc3086cc1bb0c06a4c11 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-3900000000-2d74d8232e7523f3b1c9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-fa61c6fa9a87ce4905bb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-01q9-0942200000-757da8b3406485c997b0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014i-9000000000-eac18512f2d22ab7a7ef | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-8df6d5b6cf94bf081c89 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-18079004a95c252da208 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0900000000-e6b1f9b4982e6cdc863d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-5900000000-7b9c09b3b6de28972f97 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00dl-9100000000-2ea95ead344d62e230a4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-defacc365589bc4437d7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-fd60db4d5e35794c45ae | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-001i-3900000000-fd0f1034b5c1e40435c0 | 2012-08-31 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 6031 |
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ChEMBL ID | CHEMBL58832 |
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KEGG Compound ID | C00152 |
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Pubchem Compound ID | 6267 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17196 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00174 |
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HMDB ID | HMDB00168 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCF96-C:BHH57-K |
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EAFUS ID | 261 |
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Dr. Duke ID | L-ASPARAGINE|ASPARAGINE|ASPARAGIN |
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BIGG ID | 34055 |
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KNApSAcK ID | C00001341 |
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HET ID | ASN |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1039271 |
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SuperScent ID | Not Available |
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Wikipedia ID | Asparagine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-sickling | | An agent that prevents sickling of red blood cells, used to treat sickle cell anemia by reducing hemoglobin polymerization and improving blood flow, thereby alleviating associated pain and complications. | DUKE | Diuretic | 35498 | An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Asparagine synthetase [glutamine-hydrolyzing] | ASNS | P08243 | Asparagine--tRNA ligase, cytoplasmic | NARS | O43776 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 1 | RPN1 | P04843 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase 48 kDa subunit | DDOST | P39656 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 2 | RPN2 | P04844 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3A | STT3A | P46977 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit DAD1 | DAD1 | P61803 | Isoaspartyl peptidase/L-asparaginase | ASRGL1 | Q7L266 | Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3B | STT3B | Q8TCJ2 | 60 kDa lysophospholipase | ASPG | Q86U10 | Probable asparagine--tRNA ligase, mitochondrial | NARS2 | Q96I59 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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