| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:24 UTC |
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| Update date | 2019-11-26 03:10:35 UTC |
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| Primary ID | FDB014671 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Grosheimin |
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| Description | Grosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product. |
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| CAS Number | 22489-66-3 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C15H18O4 |
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| IUPAC name | 4-hydroxy-9-methyl-3,6-dimethylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione |
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| InChI Identifier | InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3 |
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| InChI Key | YGMIBVIKXJJQQJ-UHFFFAOYSA-N |
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| Isomeric SMILES | CC1C2C3OC(=O)C(=C)C3C(O)CC(=C)C2CC1=O |
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| Average Molecular Weight | 262.301 |
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| Monoisotopic Molecular Weight | 262.120509064 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene lactones |
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| Direct Parent | Guaianolides and derivatives |
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| Alternative Parents | |
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| Substituents | - Guaianolide-skeleton
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Cyclic ketone
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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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 | Not Available |
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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 | splash10-01ot-0190000000-0540d20474782bf3fb62 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01vt-0690000000-b9b30483196b9ab2e09b | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxu-9820000000-a17e83da187ce5911fba | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0090000000-160857df66d82a2df5ec | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xu-0090000000-8c3cc5a92665e415c59e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uel-9620000000-140666a741e54aec42b3 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0090000000-da9d0d5c94a2c230a2b3 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0490000000-8e106798a130462c302d | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rj-1970000000-d72fc2dd8211965429eb | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0090000000-9e603373aa78758870d8 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0290000000-d81b674584777c7372ab | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0096-1950000000-a38d73758241fb91bfe3 | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C09472 |
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| Pubchem Compound ID | 99967 |
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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 | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | JZL91-Q:JTS60-Z |
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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 | C00003297 |
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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 | |
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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