| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:53 UTC |
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| Update date | 2019-11-26 03:00:50 UTC |
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| Primary ID | FDB005891 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Parthenolide |
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| Description | Parthenolide belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Thus, parthenolide is considered to be an isoprenoid lipid molecule. Parthenolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Parthenolide is a bitter tasting compound found in sweet bay, which makes parthenolide a potential biomarker for the consumption of this food product. Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named. It is found in highest concentration in the flowers and fruit . |
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| CAS Number | 20554-84-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Parthenolide, (1ar-(1ar*,4E,7as*,10as*,10br*))-isomer | MeSH | | (-)-parthenolide | biospider | | Feverfew 125mg | biospider | | Parthenolide | biospider |
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| Predicted Properties | |
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| Chemical Formula | C15H20O3 |
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| IUPAC name | (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one |
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| InChI Identifier | InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 |
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| InChI Key | KTEXNACQROZXEV-SLXBATTESA-N |
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| Isomeric SMILES | C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1 |
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| Average Molecular Weight | 248.3175 |
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| Monoisotopic Molecular Weight | 248.141244506 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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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 | Germacranolides and derivatives |
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| Alternative Parents | |
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| Substituents | - Germacranolide
- Germacrane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | Not Available | |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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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 | Parthenolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-6960000000-5c1aa0cf39755985bca4 | 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 | splash10-0002-0190000000-2684c1a3def8a4a69519 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-3790000000-8a7aea26cf89a7dd3c20 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxu-9200000000-455b7641ab6a4f2dd513 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-e731516f7092e30f24f4 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f6t-0190000000-ad0cc1643ecd2864122e | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zi1-9610000000-42285f97b7fa82676424 | 2017-07-26 | 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 | C07609 |
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| Pubchem Compound ID | 6473881 |
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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 | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | PARTHENOLIDE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003345 |
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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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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| 5-hydroxytryptamine inhibitor | 48279 | Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. | DUKE | | 5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | allelopathic | | | DUKE | | allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | | anti aggregant | | | DUKE | | anti arthritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti migraine | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti neuralgic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti prostaglandin | 49020 | A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. | DUKE | | anti secretory | | | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | candidicide | | | DUKE | | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | dermatitigenic | | | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | Gram(+)icide | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | hypercalcuric | | | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | phospholipase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | prostaglandin-synthetase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE |
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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 | | Flavor | Citations |
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| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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