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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-12 20:29:18 UTC |
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Update Date | 2020-02-26 21:24:36 UTC |
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HMDB ID | HMDB0003417 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Cysteine |
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Description | D-Cysteine, also known as D-cystein or DCY, 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. It is a non-proteogenic sulfur-containing amino acid. D-Cysteine is known to be toxic to bacteria and several bacteria (and plants) have developed and enzyme called D-cysteine desulfhydrase (EC4.1.99.4). D-cysteine can be generated from D-Cysteine via cysteine racemase. D-Cysteine is a naturally occurring enantiomer of L-Cysteine. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder − cystine was first isolated from kidney stones. D-Cysteine is a very strong basic compound (based on its pKa). D-Cysteine exists in all living species, ranging from bacteria to humans. Outside of the human body, D-Cysteine has been detected, but not quantified in, several different foods, such as chervils, fruits, lichee, nuts, and cherimoya. This could make D-cysteine a potential biomarker for the consumption of these foods. This enzyme decomposes D-cysteine into pyruvate, H2S, and NH3. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-Amino-3-mercaptopropanoic acid | ChEBI | (2S)-2-Amino-3-sulfanylpropanoic acid | ChEBI | (S)-2-Amino-3-mercaptopropanoic acid | ChEBI | D-Amino-3-mercaptopropionic acid | ChEBI | D-Cystein | ChEBI | D-Zystein | ChEBI | DCY | ChEBI | (2S)-2-Amino-3-mercaptopropanoate | Generator | (2S)-2-Amino-3-sulfanylpropanoate | Generator | (2S)-2-Amino-3-sulphanylpropanoate | Generator | (2S)-2-Amino-3-sulphanylpropanoic acid | Generator | (S)-2-Amino-3-mercaptopropanoate | Generator | D-Amino-3-mercaptopropionate | Generator | Cysteine | HMDB | Half cystine | HMDB | Cysteine hydrochloride | HMDB | Half-cystine | HMDB | L-Cysteine | HMDB | L Cysteine | HMDB | Zinc cysteinate | HMDB |
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Chemical Formula | C3H7NO2S |
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Average Molecular Weight | 121.15 |
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Monoisotopic Molecular Weight | 121.019749643 |
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IUPAC Name | (2S)-2-amino-3-sulfanylpropanoic acid |
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Traditional Name | L cysteine |
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CAS Registry Number | 921-01-7 |
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SMILES | N[C@H](CS)C(O)=O |
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InChI Identifier | InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 |
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InChI Key | XUJNEKJLAYXESH-UWTATZPHSA-N |
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Chemical Taxonomy |
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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
- D-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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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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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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004l-9100000000-4553906a941a5e87ec97 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-004i-9200000000-cfaf705cd0452d428454 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-056r-9300000000-ed3d829a54e4ac06325d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0a4i-9000000000-224425097c9b1883d266 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0a4i-9000000000-39cb21d5fd8f893ba8fd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00b9-9600000000-4352a7b437c34c04d9f0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9200000000-7b4cd034c717561c61dd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-8f351cbca6ffed356a9b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-6900000000-51ba0df80cc33423420b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-9400000000-4aa2b707c391d5838d29 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9000000000-95c7672c7836c0fc51c9 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Saliva | Detected and Quantified | 8.643 +/- 2.11 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB03201 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023168 |
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KNApSAcK ID | C00007323 |
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Chemspider ID | 83819 |
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KEGG Compound ID | C00793 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cysteine |
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METLIN ID | Not Available |
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PubChem Compound | 92851 |
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PDB ID | Not Available |
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ChEBI ID | 16375 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Tsukamoto S, Kanegae T, Nagoya T, Shimamura M, Mieda Y, Nomura M, Hojo K, Okubo H: Effects of amino acids on acute alcohol intoxication in mice--concentrations of ethanol, acetaldehyde, acetate and acetone in blood and tissues. Arukoru Kenkyuto Yakubutsu Ison. 1990 Oct;25(5):429-40. [PubMed:2275637 ]
- Riemenschneider A, Wegele R, Schmidt A, Papenbrock J: Isolation and characterization of a D-cysteine desulfhydrase protein from Arabidopsis thaliana. FEBS J. 2005 Mar;272(5):1291-304. [PubMed:15720402 ]
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