| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-26 05:44:02 UTC |
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| Update Date | 2016-11-09 01:21:18 UTC |
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| Accession Number | CHEM035402 |
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| Identification |
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| Common Name | Homocysteine thiolactone |
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| Class | Small Molecule |
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| Description | Homocysteine thiolactone, also known as ( -)-3-amino-2-thiolanon, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Homocysteine thiolactone is possibly soluble (in water) and a very strong basic compound (based on its pKa). |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| ( -)-3-amino-2-Thiolanon | HMDB | | ( -)-3-aminotetrahydro-2-Thiophenon | HMDB | | (+-)-3-aminodihydro-2(3H)-Thiophenone | HMDB | | 3-aminodihydro-2(3H)-Thiophenone | HMDB | | DL-3-aminotetrahydro-2-Thiophenone | HMDB | | DL-Homocysteine thiolactone | HMDB | | L-Homocysteine thiolactone | HMDB |
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| Chemical Formula | C4H7NOS |
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| Average Molecular Mass | 117.169 g/mol |
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| Monoisotopic Mass | 117.025 g/mol |
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| CAS Registry Number | 3622-59-1 |
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| IUPAC Name | 3-aminothiolan-2-one |
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| Traditional Name | DL-homocysteine thiolactone |
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| SMILES | NC1CCSC1=O |
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| InChI Identifier | InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2 |
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| InChI Key | KIWQWJKWBHZMDT-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
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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 | Alpha amino acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Alpha-amino acid or derivatives
- Thiolane
- Carbothioic s-lactone
- Thiocarboxylic acid ester
- Thiolactone
- Thiocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Hydrocarbon derivative
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6u-9000000000-7b8e6410972444b84efc | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-8f683c9002bf43fef10d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0076-9000000000-e26ebbd2d16a1aed5801 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-649e7b0f78d61a745b45 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-806166a012352ec0be63 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aba-9000000000-a8839b6dcc9998e5eadc | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0080-9000000000-97c8bd4bc30856bdda2e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-3900000000-a86fe79188b92a0f513e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-053r-9100000000-bed3e8f03e106eedf1a8 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9000000000-cfcd40acf2ab07b3f5f3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014l-6900000000-587ed663ed27e0d79f57 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9600000000-974a58cb3346970c79ff | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052o-9000000000-4073e682ce58bd088e4e | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0002287 |
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| FooDB ID | FDB022949 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 6594 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 96881 |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 107712 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. | | 2. Takehara, Jun; Ichikawa, Shuji; Iwane, Hiroshi. Preparation of DL-homocysteine thiolactone inorganic acid salts. Jpn. Kokai Tokkyo Koho (1998), 4 pp. | | 3. Ricci G, Santoro L, Achilli M, Matarese RM, Nardini M, Cavallini D: Similarity of the oxidation products of L-cystathionine by L-amino acid oxidase to those excreted by cystathioninuric patients. J Biol Chem. 1983 Sep 10;258(17):10511-7. | | 4. Jakubowski H: Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S. | | 5. Jakubowski H: Protein homocysteinylation: possible mechanism underlying pathological consequences of elevated homocysteine levels. FASEB J. 1999 Dec;13(15):2277-83. | | 6. Kerkeni M, Addad F, Chauffert M, Chuniaud L, Miled A, Trivin F, Maaroufi K: Hyperhomocysteinemia, paraoxonase activity and risk of coronary artery disease. Clin Biochem. 2006 Aug;39(8):821-5. Epub 2006 Jun 7. | | 7. Chwatko G, Jakubowski H: The determination of homocysteine-thiolactone in human plasma. Anal Biochem. 2005 Feb 15;337(2):271-7. | | 8. Jakubowski H: Pathophysiological consequences of homocysteine excess. J Nutr. 2006 Jun;136(6 Suppl):1741S-1749S. |
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