Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-10 23:58:05 UTC |
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Update Date | 2021-09-26 22:56:20 UTC |
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HMDB ID | HMDB0246945 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | alpha-Methylene-gamma-butyrolactone |
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Description | alpha-Methylene-gamma-butyrolactone, also known as α-methylidene-γ-butyrolactone or tulipalin a, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review very few articles have been published on alpha-Methylene-gamma-butyrolactone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-methylene-gamma-butyrolactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-Methylene-gamma-butyrolactone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2 |
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Synonyms | Value | Source |
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3-Methylenedihydro-2(3H)-furanone | ChEBI | alpha-Methylene butyrolactone | ChEBI | alpha-Methylidene-gamma-butyrolactone | ChEBI | Dihydro-3-methylene-2(3H)-furanone | ChEBI | Tulipalin a | ChEBI | 2-Methylenebutanolactone | Kegg | a-Methylene butyrolactone | Generator | Α-methylene butyrolactone | Generator | a-Methylidene-g-butyrolactone | Generator | Α-methylidene-γ-butyrolactone | Generator | a-Methylene-g-butyrolactone | Generator | Α-methylene-γ-butyrolactone | Generator | a-Methylene g-butyrolactone | HMDB | Α-methylene γ-butyrolactone | HMDB | alpha-Methylene gamma-butyrolactone | HMDB | alpha-Methylene-gamma-butyrolactone | ChEBI |
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Chemical Formula | C5H6O2 |
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Average Molecular Weight | 98.101 |
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Monoisotopic Molecular Weight | 98.036779433 |
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IUPAC Name | 3-methylideneoxolan-2-one |
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Traditional Name | tulipalin A |
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CAS Registry Number | Not Available |
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SMILES | C=C1CCOC1=O |
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InChI Identifier | InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2 |
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InChI Key | GSLDEZOOOSBFGP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Gamma butyrolactones |
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Direct Parent | Gamma butyrolactones |
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Alternative Parents | |
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Substituents | - Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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alpha-Methylene-gamma-butyrolactone | C=C1CCOC1=O | 1660.0 | Standard polar | 33892256 | alpha-Methylene-gamma-butyrolactone | C=C1CCOC1=O | 835.9 | Standard non polar | 33892256 | alpha-Methylene-gamma-butyrolactone | C=C1CCOC1=O | 1050.9 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylene-gamma-butyrolactone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udj-9000000000-487f83d08065695034c9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylene-gamma-butyrolactone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 10V, Positive-QTOF | splash10-0002-9000000000-c45d8f2f7586116bdfee | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 20V, Positive-QTOF | splash10-0002-9000000000-a8073757d03d8ba3677a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 40V, Positive-QTOF | splash10-0zfr-9000000000-60eeed360fba53f0436e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 10V, Negative-QTOF | splash10-0002-9000000000-aaec60432819fd6b1731 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 20V, Negative-QTOF | splash10-0udj-9000000000-153ff3cfde6b44f6f0a4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 40V, Negative-QTOF | splash10-0udi-9000000000-d97023c0ff6e34caf786 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 10V, Positive-QTOF | splash10-052b-9000000000-cc2bb18b6b015369905f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 20V, Positive-QTOF | splash10-0zfu-9000000000-8fcfaace5e4a8c70b5df | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 40V, Positive-QTOF | splash10-0udi-9000000000-76bd7b6c1c60870b5419 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 10V, Negative-QTOF | splash10-0002-9000000000-dbbfc6dec07aeb7b66c0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 20V, Negative-QTOF | splash10-0uxs-9000000000-5bc5e4d0490a3ce71e63 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylene-gamma-butyrolactone 40V, Negative-QTOF | splash10-0f6x-9000000000-260134a476cb143d08e2 | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | 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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | C00040580 |
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Chemspider ID | 61647 |
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KEGG Compound ID | C20578 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 68352 |
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PDB ID | Not Available |
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ChEBI ID | 104120 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1218461 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
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