Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:18 UTC |
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Update date | 2020-09-17 15:38:37 UTC |
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Primary ID | FDB012678 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Cysteine |
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Description | L-Cysteine, also known as C or e 920, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine is a very strong basic compound (based on its pKa). L-Cysteine exists in all living species, ranging from bacteria to humans. Within humans, L-cysteine participates in a number of enzymatic reactions. In particular, L-cysteine can be converted into 3-sulfinoalanine; which is mediated by the enzyme cysteine dioxygenase type 1. In addition, L-cysteine can be converted into hydrogen sulfide and pyruvic acid through the action of the enzyme cystathionine gamma-lyase. In humans, L-cysteine is involved in cysteine metabolism. L-Cysteine is a sulfury tasting compound. Outside of the human body, L-Cysteine is found, on average, in the highest concentration within a few different foods, such as sunflowers, soy beans, and watermelons and in a lower concentration in common wheats, dates, and beers. L-Cysteine has also been detected, but not quantified in, several different foods, such as oyster mushrooms, salmonberries, rapes, safflowers, and cupuaçus. This could make L-cysteine a potential biomarker for the consumption of these foods. L-Cysteine is a potentially toxic compound. An optically active form of cysteine having L-configuration. |
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CAS Number | 52-90-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(2R)-2-Amino-3-mercaptopropanoic acid | ChEBI | (2R)-2-Amino-3-sulfanylpropanoic acid | ChEBI | (R)-2-Amino-3-mercaptopropanoic acid | ChEBI | C | ChEBI | Cys | ChEBI | CYSTEINE | ChEBI | e 920 | ChEBI | e-920 | ChEBI | e920 | ChEBI | FREE cysteine | ChEBI | L-2-Amino-3-mercaptopropionic acid | ChEBI | L-Cystein | ChEBI | L-Zystein | ChEBI | Ecolan | Kegg | (2R)-2-Amino-3-mercaptopropanoate | Generator | (2R)-2-Amino-3-sulfanylpropanoate | Generator | (2R)-2-Amino-3-sulphanylpropanoate | Generator | (2R)-2-Amino-3-sulphanylpropanoic acid | Generator | (R)-2-Amino-3-mercaptopropanoate | Generator | L-2-Amino-3-mercaptopropionate | Generator | (+)-2-Amino-3-mercaptopropionic acid | HMDB | (R)-(+)-Cysteine | HMDB | (R)-2-Amino-3-mercapto-propanoate | HMDB | (R)-2-Amino-3-mercapto-propanoic acid | HMDB | (R)-Cysteine | HMDB | 2-Amino-3-mercaptopropanoate | HMDB | 2-Amino-3-mercaptopropanoic acid | HMDB | 2-Amino-3-mercaptopropionate | HMDB | 2-Amino-3-mercaptopropionic acid | HMDB | 3-Mercapto-L-alanine | HMDB | Acetylcysteine | HMDB | alpha-Amino-beta-thiolpropionic acid | HMDB | b-Mercaptoalanine | HMDB | beta-Mercaptoalanine | HMDB | Carbocysteine | HMDB | Cisteina | HMDB | Cisteinum | HMDB | Cystein | HMDB | Cysteinum | HMDB | Half-cystine | HMDB | L Cysteine | HMDB | L-(+)-Cysteine | HMDB | L-2-Amino-3-mercaptopropanoate | HMDB | L-2-Amino-3-mercaptopropanoic acid | HMDB | Polycysteine | HMDB | Thioserine | HMDB | Cysteine hydrochloride | HMDB | Zinc cysteinate | HMDB | Half cystine | HMDB | (2R)-2-amino-3-Sulphanylpropanoate | Generator | (2R)-2-amino-3-Sulphanylpropanoic acid | Generator | (R)-2-Amino-3-mercaptopropionic acid | biospider | α-amino-β-Thiolpropionic acid | biospider | β-Mercaptoalanine | biospider | 2-Amino-3-mercapto-, (R)- | biospider | 2-Amino-3-mercaptopropanoic acid, (R)- | biospider | 3-Mercapto-L-Alanine | biospider | alpha-Amino-beta-mercaptopropanoic acid, L- | biospider | alpha-Amino-beta-mercaptopropionic acid, L- | biospider | alpha-Amino-beta-thiolpropionic acid, L- | biospider | beta-Mercaptoalanine, L- | biospider | CYS | biospider | Cysteine | biospider | Cysteine, INN; L-form | db_source | Ecolan (TN) | biospider | L-2-amino-3-Mercaptopropionate | Generator | L-Alanine, 3-mercapto- | biospider | L-CYS | biospider | L-Cysteine | biospider | Propanoic Acid, 2-amino-3-mercapto-, (R)- | biospider |
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Predicted Properties | Not Available |
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Chemical Formula | C3H7NO2S |
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IUPAC name | |
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InChI Identifier | InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 |
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InChI Key | XUJNEKJLAYXESH-REOHCLBHSA-N |
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Isomeric SMILES | N[C@@H](CS)C(O)=O |
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Average Molecular Weight | 121.158 |
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Monoisotopic Molecular Weight | 121.019749163 |
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Classification |
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Description | Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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 | Cysteine and derivatives |
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Alternative Parents | |
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Substituents | - Cysteine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Amino acid
- Alkylthiol
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- 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 | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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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 29.74%; H 5.82%; N 11.56%; O 26.41%; S 26.47% | DFC |
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Melting Point | Mp 178° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 277 mg/mL at 25 oC | BEILSTEIN |
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Experimental logP | -2.49 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa3 10.46 (SH) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D +26.5 (5M 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-Cysteine, 4 TMS, GC-MS Spectrum | splash10-00kb-0950000000-df7e91c95b610ff21c79 | Spectrum | GC-MS | L-Cysteine, 4 TMS, GC-MS Spectrum | splash10-00kb-0940000000-aefe34765fb447090a23 | Spectrum | GC-MS | L-Cysteine, 4 TMS, GC-MS Spectrum | splash10-00kb-0970000000-10a155c40ea499023052 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00kb-0940000000-037a3a34651c3154b3b3 | Spectrum | GC-MS | L-Cysteine, 4 TMS, GC-MS Spectrum | splash10-00di-9850000000-118c43e33861a6baa8d2 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-014j-0690100000-0aeb88fd507505e6b718 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00kb-0950000000-df7e91c95b610ff21c79 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00kb-0940000000-aefe34765fb447090a23 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00kb-0970000000-10a155c40ea499023052 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00kb-0940000000-037a3a34651c3154b3b3 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-0uk9-5619100000-8cb2558373966174ced3 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-00di-9850000000-118c43e33861a6baa8d2 | Spectrum | GC-MS | L-Cysteine, non-derivatized, GC-MS Spectrum | splash10-0gi0-0960000000-03b2097de6f9637d29cb | Spectrum | Predicted GC-MS | L-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004l-9100000000-4553906a941a5e87ec97 | Spectrum | Predicted GC-MS | L-Cysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-9200000000-cfaf705cd0452d428454 | Spectrum | Predicted GC-MS | L-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Cysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Cysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Cysteine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Cysteine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Cysteine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | 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) | splash10-00b9-9600000000-374c5872d68662832769 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-9000000000-ddbd3df6b8dbb280ffba | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-9000000000-320a2c77443b80ebf733 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0089-0900000000-9dcd3d757c5cd11eb18e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-3900000000-212e081fe83ad70de0ad | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-2eb01f41c225f614db24 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-a19834eb7cb9f211fdf2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-2458f2587761e779ed93 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-9000000000-77e590f0ed26f69b31c0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-3900000000-7b1857997392b006b95f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-3900000000-bc268c27ed5706a4bbd2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive | splash10-00di-0900000000-4573390bccc238e3c91b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-3900000000-212e081fe83ad70de0ad | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-3900000000-7b1857997392b006b95f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 14V, negative | splash10-001i-9000000000-5dc69d3b59bd15290aef | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0a6r-9100000000-ed3c9c47ed98679090ab | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-00di-2900000000-8bb219d17ccdf7ac0a5d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0a4i-9000000000-e623d5a27b5075c82b4d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-056r-9100000000-4e26cc13af7c878115f7 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00b9-9600000000-4352a7b437c34c04d9f0 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9200000000-7b4cd034c717561c61dd | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-8f351cbca6ffed356a9b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-6900000000-51ba0df80cc33423420b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-9400000000-4aa2b707c391d5838d29 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9000000000-95c7672c7836c0fc51c9 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 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 | 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 | 5653 |
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ChEMBL ID | CHEMBL863 |
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KEGG Compound ID | C00097 |
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Pubchem Compound ID | 5862 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17561 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00151 |
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HMDB ID | HMDB00574 |
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CRC / DFC (Dictionary of Food Compounds) ID | HJQ86-N:HJQ81-I |
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EAFUS ID | 813 |
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Dr. Duke ID | CYSTEINE |
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BIGG ID | 33843 |
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KNApSAcK ID | C00001351 |
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HET ID | CYS |
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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 | rw1018061 |
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SuperScent ID | Not Available |
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Wikipedia ID | L-Cysteine |
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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 | |
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Enzymes | Name | Gene Name | UniProt ID |
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Aspartate aminotransferase, cytoplasmic | GOT1 | P17174 | Aspartate aminotransferase, mitochondrial | GOT2 | P00505 | Glutathione synthetase | GSS | P48637 | Molybdenum cofactor sulfurase | MOCOS | Q96EN8 | Glutamate--cysteine ligase catalytic subunit | GCLC | P48506 | Cystathionine gamma-lyase | CTH | P32929 | Cysteine sulfinic acid decarboxylase | CSAD | Q9Y600 | Gamma-glutamylcyclotransferase | GGCT | O75223 | Phosphopantothenate--cysteine ligase | PPCS | Q9HAB8 | Glutamate--cysteine ligase regulatory subunit | GCLM | P48507 | Thiamine transporter 2 | SLC19A3 | Q9BZV2 | Cysteine--tRNA ligase, cytoplasmic | CARS | P49589 | Cysteine dioxygenase | CDO-1 | Q16857 |
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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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sulfury |
- 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). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
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