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Identification |
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YMDB ID | YMDB00226 |
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Name | L-Asparagine |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Asparagine (abbreviated as Asn or N) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a polar amino acid, because of the hydrophilic nature of its alkyl-amide or alkyl-carboxamide side chain. Asparagine can be considered the amide of aspartic acid The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. Glutamine donates an ammonium group, which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Aspartate is a glucogenic amino acid. L-asparaginase hydrolyzes the amide group to form aspartate and ammonium. A transaminase converts the aspartate to oxaloacetate, which can then be metabolized in the citric acid cycle or gluconeogenesis. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature. These products occur in baked goods such as French fries, potato chips, and roasted coffee. |
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Structure | |
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Synonyms | - (-)-Asparagine
- (S)-2,4-Diamino-4-oxobutanoate
- (S)-2,4-Diamino-4-oxobutanoic acid
- (S)-Asparagine
- 2-Aminosuccinamate
- 2-Aminosuccinamic acid
- a-Aminosuccinamate
- a-Aminosuccinamic acid
- Agedoite
- alpha Amminosuccinamate
- alpha Amminosuccinamic acid
- alpha-Aminosuccinamate
- alpha-Aminosuccinamic acid
- Altheine
- Asn
- Asparagine
- Asparagine acid
- Asparamide
- Aspartamate
- Aspartamic acid
- Aspartic acid amide
- Aspartic acid b-amide
- Aspartic acid beta amide
- B2,4-(S)-diamino-4-oxo-utanoate
- B2,4-(S)-diamino-4-oxo-utanoic acid
- L-2,4-Diamino-4-oxobutanoate
- L-2,4-Diamino-4-oxobutanoic acid
- l-Asparagine
- L-Aspartamine
- L-b-Asparagine
- L-beta-Asparagine
- (2S)-2,4-Diamino-4-oxobutanoic acid
- (2S)-2-Amino-3-carbamoylpropanoic acid
- (S)-2-Amino-3-carbamoylpropanoic acid
- L-2-Aminosuccinamic acid
- L-Asparagin
- L-Aspartic acid beta-amide
- N
- (2S)-2,4-Diamino-4-oxobutanoate
- (2S)-2-Amino-3-carbamoylpropanoate
- (S)-2-Amino-3-carbamoylpropanoate
- Α-aminosuccinamate
- Α-aminosuccinamic acid
- L-2-Aminosuccinamate
- L-Aspartate b-amide
- L-Aspartate beta-amide
- L-Aspartate β-amide
- L-Aspartic acid b-amide
- L-Aspartic acid β-amide
- Crystal VI
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CAS number | 70-47-3 |
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Weight | Average: 132.1179 Monoisotopic: 132.053492132 |
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InChI Key | DCXYFEDJOCDNAF-REOHCLBHSA-N |
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InChI | 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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IUPAC Name | (2S)-2-amino-3-carbamoylpropanoic acid |
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Traditional IUPAC Name | L-asparagine |
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Chemical Formula | C4H8N2O3 |
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SMILES | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C(=O)N([H])[H] |
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Chemical Taxonomy |
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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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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 234-235 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 29.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP | -3.82 [CHMELIK,J ET AL. (1991)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - extracellular
- mitochondrion
- vacuole
- cytoplasm
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | Alanine, aspartate and glutamate metabolism | ec00250 |  | Cyanoamino acid metabolism | ec00460 |  | Nitrogen metabolism | ec00910 |  |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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427 ± 21 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined Not Available | 820 ± 116 µM | Synthetic medium with 20 g/L glucose | aerobic | Baker's yeast | PMID: 12584756 | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0159-0910000000-bedf57998656ab5ebc16 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-0159-0910000000-4979c4d028d2dc931263 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0159-0910000000-b7ea3fef61f3940cbdda | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-9710000000-6d0afcbcc003347e598e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0uxr-0910000000-2be567239bd3229b1ca1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-02t9-0790000000-b8141f48cbebb90f683e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-02t9-1790000000-1d12ed9b4fb2799da766 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-014u-0961000000-65a5c0999f17110c9939 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-00lr-1920000000-7864dbb1f685e64dd1cf | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-000i-1940000000-964ea25da2789805985a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00lr-0930000000-79a089d9875e092dd7f2 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-bedf57998656ab5ebc16 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-4979c4d028d2dc931263 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-b7ea3fef61f3940cbdda | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-00di-4931100000-17f149310ce3a0f748d1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9710000000-6d0afcbcc003347e598e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0uxr-0910000000-2be567239bd3229b1ca1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-02t9-0790000000-b8141f48cbebb90f683e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-02t9-1790000000-1d12ed9b4fb2799da766 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014u-0961000000-65a5c0999f17110c9939 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00lr-1920000000-7864dbb1f685e64dd1cf | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000i-1940000000-964ea25da2789805985a | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000f-9100000000-5881591331bd059b7e7d | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0080-9400000000-e5c7e19f427eea6d71b0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-afc1214100db1168b095 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00dl-9000000000-57e977cd87e9a86d482b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-6fb96f5aa291359dba29 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-76f11e6fe5657c35d15f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-e944486273dbfde4cae4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-27ad91a86be0c4d86c3c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-b8b7a3431b66246ad613 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-03fa294ec740e189dd99 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-cee2081406fc25ab6169 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-cd79afa0c27f65e54adc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-01q9-0943200000-5a24322ba0ce2f410155 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-fc3086cc1bb0c06a4c11 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-3900000000-2d74d8232e7523f3b1c9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-fa61c6fa9a87ce4905bb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-01q9-0942200000-757da8b3406485c997b0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014i-9000000000-eac18512f2d22ab7a7ef | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-8df6d5b6cf94bf081c89 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-18079004a95c252da208 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0900000000-e6b1f9b4982e6cdc863d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-5900000000-7b9c09b3b6de28972f97 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00dl-9100000000-2ea95ead344d62e230a4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-defacc365589bc4437d7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-fd60db4d5e35794c45ae | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-001i-3900000000-fd0f1034b5c1e40435c0 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
- Zhu, X., Garrett, J., Schreve, J., Michaeli, T. (1996). "GNP1, the high-affinity glutamine permease of S. cerevisiae." Curr Genet 30:107-114.8660458
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Synthesis Reference: | Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp. |
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External Links: | |
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