| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:22:14 UTC |
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| Update date | 2019-11-26 03:21:06 UTC |
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| Primary ID | FDB022949 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Homocysteine thiolactone |
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| Description | Elevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349)
The only known source of Hcy in the human body is dietary protein methionine; subsequent examinations of individual dietary amino acids have led to the conclusion that methionine, ingested in excess, is the most toxic amino acid.
(Harper AE, Benevenga NJ, Wohlheuter RM. Effects of ingestion of disproportionate amounts of amino acids. Physiol Rev. 1970;50: 428 - 58; Benevenga NJ, Steele RD. Adverse effects of excessive consumption of amino acids. Annu Rev Nutr. 1984; 4:157-81)
Animals fed high-protein or high-methionine diets for 2 years developed hyperhomocysteinemia and evidence of vascular disease (Fau D, Preret J, Hadjiisky P. Effects of ingestion of high protein or excess methionine diets by rats for two years. J Nutr. 1988; 118:128-33) [HMDB] |
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| CAS Number | 3622-59-1 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C4H7NOS |
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| IUPAC name | 3-aminothiolan-2-one |
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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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| Isomeric SMILES | NC1CCSC1=O |
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| Average Molecular Weight | 117.169 |
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| Monoisotopic Molecular Weight | 117.024834541 |
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| Classification |
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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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| Ontology |
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| Disposition | Biological location: Source: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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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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| Predicted GC-MS | Homocysteine thiolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a6u-9000000000-7b8e6410972444b84efc | Spectrum | | Predicted GC-MS | Homocysteine thiolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Homocysteine thiolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-8f683c9002bf43fef10d | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0076-9000000000-e26ebbd2d16a1aed5801 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-649e7b0f78d61a745b45 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-806166a012352ec0be63 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aba-9000000000-a8839b6dcc9998e5eadc | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0080-9000000000-97c8bd4bc30856bdda2e | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-3900000000-a86fe79188b92a0f513e | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-053r-9100000000-bed3e8f03e106eedf1a8 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9000000000-cfcd40acf2ab07b3f5f3 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014l-6900000000-587ed663ed27e0d79f57 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9600000000-974a58cb3346970c79ff | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052o-9000000000-4073e682ce58bd088e4e | 2021-09-22 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 96881 |
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| ChEMBL ID | CHEMBL3272518 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 107712 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02287 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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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 | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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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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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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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 | Not Available |
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| Files |
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| MSDS | Not Available |
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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 | |
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