| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-05-22 04:27:33 UTC |
|---|
| Update Date | 2016-11-09 01:15:37 UTC |
|---|
| Accession Number | CHEM017552 |
|---|
| Identification |
|---|
| Common Name | Parthenolide |
|---|
| Class | Small Molecule |
|---|
| Description | 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. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available. The structure depicted here is the correct one. |
|---|
| Contaminant Sources | - FooDB Chemicals
- ToxCast & Tox21 Chemicals
|
|---|
| Contaminant Type | Not Available |
|---|
| Chemical Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| Parthenolide, (1ar-(1ar*,4E,7as*,10as*,10br*))-isomer | MeSH |
|
|---|
| Chemical Formula | C15H20O3 |
|---|
| Average Molecular Mass | 248.322 g/mol |
|---|
| Monoisotopic Mass | 248.141 g/mol |
|---|
| CAS Registry Number | 20554-84-1 |
|---|
| IUPAC Name | (1S,2S,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one |
|---|
| Traditional Name | parthenolide |
|---|
| SMILES | [H]\C1=C(C)\CC[C@@]2([H])C(=C)C(=O)O[C@]2([H])[C@]2([H])O[C@]2(C)CC1 |
|---|
| 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 |
|---|
| InChI Key | KTEXNACQROZXEV-QLIGOWBFSA-N |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Terpene lactones |
|---|
| Direct Parent | Germacranolides and derivatives |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aliphatic heteropolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Biological Properties |
|---|
| Status | Detected and Not Quantified |
|---|
| Origin | Not Available |
|---|
| Cellular Locations | Not Available |
|---|
| Biofluid Locations | Not Available |
|---|
| Tissue Locations | Not Available |
|---|
| Pathways | Not Available |
|---|
| Applications | Not Available |
|---|
| Biological Roles | Not Available |
|---|
| Chemical Roles | Not Available |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Appearance | Not Available |
|---|
| Experimental Properties | | Property | Value |
|---|
| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0190000000-2684c1a3def8a4a69519 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-3790000000-8a7aea26cf89a7dd3c20 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxu-9200000000-455b7641ab6a4f2dd513 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-e731516f7092e30f24f4 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f6t-0190000000-ad0cc1643ecd2864122e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zi1-9610000000-42285f97b7fa82676424 | Spectrum |
|
|---|
| Toxicity Profile |
|---|
| Route of Exposure | Not Available |
|---|
| Mechanism of Toxicity | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Toxicity Values | Not Available |
|---|
| Lethal Dose | Not Available |
|---|
| Carcinogenicity (IARC Classification) | Not Available |
|---|
| Uses/Sources | Not Available |
|---|
| Minimum Risk Level | Not Available |
|---|
| Health Effects | Not Available |
|---|
| Symptoms | Not Available |
|---|
| Treatment | Not Available |
|---|
| Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | Not Available |
|---|
| FooDB ID | Not Available |
|---|
| Phenol Explorer ID | Not Available |
|---|
| KNApSAcK ID | Not Available |
|---|
| BiGG ID | Not Available |
|---|
| BioCyc ID | Not Available |
|---|
| METLIN ID | Not Available |
|---|
| PDB ID | Not Available |
|---|
| Wikipedia Link | Parthenolide |
|---|
| Chemspider ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| PubChem Compound ID | 5420805 |
|---|
| Kegg Compound ID | Not Available |
|---|
| YMDB ID | Not Available |
|---|
| ECMDB ID | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| MSDS | Not Available |
|---|
| General References | Not Available |
|---|
