Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-11 17:41:56 UTC |
---|
Update Date | 2023-02-21 17:20:12 UTC |
---|
HMDB ID | HMDB0031257 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Dimethyl fumarate |
---|
Description | Dimethyl fumarate is a fungal growth inhibitor for tomato juice Dimethyl fumarate is an ester and an , -unsaturated electrophilic compound, undergoing reactions typical to them. It is also a diene acceptor in the ordinary Diels-Alder reaction, where the reactivity of its vinylidenic bond is enchanced by the two electron-withdrawing ester groups. Due to the geometry of the starting ester, the Diels-Alder product will have a trans configuration. Dimethyl fumarate is used to treat psoriasis. It is a lipophilic, highly mobile molecule in human tissue. However, as an , -unsaturated ester, dimethyl fumarate reacts rapidly with the detoxifying agent glutathione by Michael addition. When administered orally, it does not survive long enough to be absorbed into blood |
---|
Structure | InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ |
---|
Synonyms | Value | Source |
---|
(e)-But-2-enedioic acid dimethyl ester | ChEBI | 1,2-Bis(methoxycarbonyl)-trans-ethylene | ChEBI | Dimethyl trans-ethylenedicarboxylate | ChEBI | Fumaric acid, dimethyl ester | ChEBI | Tecfidera | ChEBI | trans-1,2-Ethylenedicarboxylic acid dimethyl ester | ChEBI | trans-Butenedioic acid dimethyl ester | ChEBI | (e)-But-2-enedioate dimethyl ester | Generator | Dimethyl trans-ethylenedicarboxylic acid | Generator | Fumarate, dimethyl ester | Generator | trans-1,2-Ethylenedicarboxylate dimethyl ester | Generator | trans-Butenedioate dimethyl ester | Generator | Dimethyl fumaric acid | Generator | 2-Butenedioic acid, (2E)-, dimethyl ester | HMDB | Fumarate, dimethyl | HMDB | Dimethylfumarate | HMDB |
|
---|
Chemical Formula | C6H8O4 |
---|
Average Molecular Weight | 144.1253 |
---|
Monoisotopic Molecular Weight | 144.042258744 |
---|
IUPAC Name | 1,4-dimethyl (2E)-but-2-enedioate |
---|
Traditional Name | dimethyl fumarate |
---|
CAS Registry Number | 624-49-7 |
---|
SMILES | COC(=O)\C=C\C(=O)OC |
---|
InChI Identifier | InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ |
---|
InChI Key | LDCRTTXIJACKKU-ONEGZZNKSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acid esters |
---|
Direct Parent | Fatty acid esters |
---|
Alternative Parents | |
---|
Substituents | - Fatty acid ester
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Not Available | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | |
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-03di-9600000000-85c5795d39a711edce4a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-03di-9500000000-ef1a2c817c752048ca3d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-014i-6900000000-b4104322040a20afbf87 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-03di-9500000000-38079515fe54a7a128d6 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-03di-9500000000-8e3b99fc3ddb06539d43 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl fumarate EI-B (Non-derivatized) | splash10-03di-9800000000-d3ec2acefa5532f1d130 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethyl fumarate GC-MS (Non-derivatized) - 70eV, Positive | splash10-03el-9600000000-d44c916d867c4271a013 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethyl fumarate 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 |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 10V, Positive-QTOF | splash10-01ot-0900000000-52a1c7b06f3e21edf137 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 20V, Positive-QTOF | splash10-01ot-3900000000-2c7c53ab39a3c1688bac | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 40V, Positive-QTOF | splash10-06sr-9200000000-509f89775c164df76c24 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 10V, Negative-QTOF | splash10-0006-0900000000-40c63012b9511f8490e3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 20V, Negative-QTOF | splash10-01ox-2900000000-c0fd047df97ddf890ee1 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 40V, Negative-QTOF | splash10-001i-9200000000-89cb0515dab9e09d5146 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 10V, Positive-QTOF | splash10-01p9-9500000000-33bc0abdab46b5a42b1f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 20V, Positive-QTOF | splash10-0k9l-9000000000-12b87d2f6c05d6047916 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 40V, Positive-QTOF | splash10-0zfr-9000000000-cc19a5706e05ef5eb348 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 10V, Negative-QTOF | splash10-03di-1900000000-1d56ae91abb29a4fba91 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 20V, Negative-QTOF | splash10-0gx0-9300000000-13e505571c984fd1ebfb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl fumarate 40V, Negative-QTOF | splash10-066r-9000000000-494ce88adb3552f6a330 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|