Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:08:57 UTC |
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Update Date | 2023-02-21 17:24:10 UTC |
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HMDB ID | HMDB0034335 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Thermophillin |
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Description | Thermophillin is found in herbs and spices. Thermophillin is isolated from Acorus calamus (sweet flag) Disulfiram produces a sensitivity to alcohol which results in a highly unpleasant reaction when the patient under treatment ingests even small amounts of alcohol. Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake, the concentration of acetaldehyde occurring in the blood may be 5 to 10 times higher than that found during metabolism of the same amount of alcohol alone. Accumulation of acetaldehyde in the blood produces a complex of highly unpleasant symptoms referred to hereinafter as the disulfiram-alcohol reaction. This reaction, which is proportional to the dosage of both disulfiram and alcohol, will persist as long as alcohol is being metabolized. Disulfiram does not appear to influence the rate of alcohol elimination from the body. Prolonged administration of disulfiram does not produce toleranc |
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Structure | InChI=1S/C8H8O4/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3 |
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Synonyms | Value | Source |
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2,5-Dimethoxy-4-benzoquinone | MeSH | 1,1',1'',1'''-[dithiobis(carbonothioylnitrilo)]tetraethane | HMDB | 1,1'-Dithiobis(N,N-diethylthio)-formamide | HMDB | 1,1'-Dithiobis(N,N-diethylthio-formamide | HMDB | 1,1'-Dithiobis(N,N-diethylthioformamide) | HMDB | 1,1'-Dithiobis[N,N-diethylthioformamide] | HMDB | 2,5-Dimethoxy-1,4-benzoquinone | HMDB | Abstenisil | HMDB | Abstensil | HMDB | Abstinil | HMDB | Abstinyl | HMDB | Accel tet | HMDB | Accel tet-R | HMDB | Alcophobin | HMDB | Alk-aubs | HMDB | Allphar brand OF disulfiram | HMDB | Altana pharma brand OF disulfiram | HMDB | Antab use | HMDB | Antabus | HMDB | Antabuse | HMDB | Antadix | HMDB | Antaenyl | HMDB | Antaethan | HMDB | Antaethyl | HMDB | Antaetil | HMDB | Antalcol | HMDB | Antetan | HMDB | Antethyl | HMDB | Antetil | HMDB | Anteyl | HMDB | Anthethyl | HMDB | Anti-ethyl | HMDB | Antiaethan | HMDB | Anticol | HMDB | Antietanol | HMDB | Antiethanol | HMDB | Antietil | HMDB | Antikol | HMDB | Antivitium | HMDB | Antivitium (spain) | HMDB | Artu brand OF disulfiram | HMDB | Aversan | HMDB | Averzan | HMDB | Bis((diethylamino)thioxomethyl) disulfide | HMDB | Bis((diethylamino)thioxomethyl)disulfide | HMDB | Bis((diethylamino)thioxomethyl)disulphide | HMDB | Bis(diethylthiocarbamoyl) disulfide | HMDB | Bis(diethylthiocarbamoyl)disulphide | HMDB | Bis(diethylthiocarbamyl) disulfide | HMDB | Bis(N,N-diethylthiocarbamoyl) disulfide | HMDB | Bis(N,N-diethylthiocarbamoyl)disulphide | HMDB | Bis-(diethylthiocarbamoyl)disulfide | HMDB | Bis[(diethylamino)thioxomethyl] disulfide | HMDB | Bohm brand OF disulfiram | HMDB | Bonibal | HMDB | Contralin | HMDB | Contrapot | HMDB | Cronetal | HMDB | Dicupral | HMDB | Diethylcarbamothioylsulfanyl diethylaminomethanedithioate | HMDB | Disetil | HMDB | Disulfamide | HMDB | Disulfan | HMDB | Disulfide, bis(diethylthiocarbamoyl) | HMDB | Disulfide, tetraethylthiuram | HMDB | Disulfiram | HMDB | Disulfiram (JP15/usp/inn) | HMDB | Disulfiram (tetraethylthiuram disulfide) | HMDB | Disulfirame | HMDB | Disulfiramo | HMDB | Disulfiramum | HMDB | Disulfirm | HMDB | Disulfuram | HMDB | Disulphuram | HMDB | Dumex brand OF disulfiram | HMDB | Dupont fungicide 4472 | HMDB | Ekagom dtet | HMDB | Ekagom teds | HMDB | Ekagom tetds | HMDB | Ephorran | HMDB | Espenal | HMDB | Esperal | HMDB | eta Bus | HMDB | Etabus | HMDB | Ethyl thiram | HMDB | Ethyl thiudad | HMDB | Ethyl thiurad | HMDB | Ethyl tuads | HMDB | Ethyl tuex | HMDB | Ethyldithiourame | HMDB | Ethyldithiurame | HMDB | Exhoran | HMDB | Exhorran | HMDB | HOCA | HMDB | Krotenal | HMDB | N,N,N',n'-tetraethylthiuram disulfide | HMDB | N,N,N',n'-tetraethylthiuram disulphide | HMDB | Nocbin | HMDB | Nocceler | HMDB | Nocceler tet | HMDB | Nocceler tet-g | HMDB | Noxal | HMDB | Odyssey brand OF disulfiram | HMDB | Orphan brand OF disulfiram | HMDB | Refusal | HMDB | ro-Sulfiram | HMDB | ro-Sulfram-500 (usa) | HMDB | Robac tet | HMDB | Sanceler tet | HMDB | Sanceler tet-g | HMDB | Sanofi synthelabo brand OF disulfiram | HMDB | Soxinol tet | HMDB | Stopaethyl | HMDB | Stopethyl | HMDB | Stopety | HMDB | Stopetyl | HMDB | TATD | HMDB | Tenurid | HMDB | Tenutex | HMDB | Tet raethylthiuram | HMDB | TETD | HMDB | Tetidis | HMDB | Tetradin | HMDB | Tetradine | HMDB | Tetraethyl-thioperoxydicarbonic diamide | HMDB | Tetraethyl-thioperoxydicarbonic diamide (((H2N)C(S))2S2) | HMDB | Tetraethyl-thioperoxydicarbonic diamide ((H2N)C(S))2S2 | HMDB | Tetraethyl-thioperoxydicarbonic diamide ([(H2N)C(S)]2S2) | HMDB | Tetraethyl-thiuram disulfide | HMDB | Tetraethylthioperoxydicarbonic diamide | HMDB | Tetraethylthioperoxydicarbonic diamide, ((H2N)C(S))2S2 | HMDB | Tetraethylthioperoxydicarbonothioic diamide | HMDB | Tetraethylthiram disulfide | HMDB | Tetraethylthiram disulphide | HMDB | Tetraethylthiuram | HMDB | Tetraethylthiuram disulfide | HMDB | Tetraethylthiuram disulphide | HMDB | Tetraethylthiuram sulfide | HMDB | Tetraethylthiuran disulfide | HMDB | Tetraethylthiurium disulfide | HMDB | Tetraetil | HMDB | Teturam | HMDB | Teturamin | HMDB | Thermophyllin | HMDB | Thiocid | HMDB | Thiosan | HMDB | Thioscabin | HMDB | Thireranide | HMDB | Thiuram e | HMDB | Thiuranide | HMDB | Tillram | HMDB | Tiuram | HMDB | TTD | HMDB | TTS | HMDB | Tuads, ethyl | HMDB |
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Chemical Formula | C8H8O4 |
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Average Molecular Weight | 168.1467 |
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Monoisotopic Molecular Weight | 168.042258744 |
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IUPAC Name | 2,5-dimethoxycyclohexa-2,5-diene-1,4-dione |
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Traditional Name | 2,5-dimethoxycyclohexa-2,5-diene-1,4-dione |
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CAS Registry Number | 3117-03-1 |
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SMILES | COC1=CC(=O)C(OC)=CC1=O |
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InChI Identifier | InChI=1S/C8H8O4/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3 |
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InChI Key | RMMPZDDLWLALLJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | P-benzoquinones |
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Alternative Parents | |
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Substituents | - P-benzoquinone
- Vinylogous ester
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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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 IndicesUnderivatized |
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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 - Thermophillin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0apu-9800000000-c8a3f9d852866bf4d4b7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Thermophillin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Thermophillin 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 - Thermophillin 10V, Positive-QTOF | splash10-014i-0900000000-4a3fba5f0011ea9f9d8b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 20V, Positive-QTOF | splash10-014i-0900000000-d05753c66ba20e3fb5e1 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 40V, Positive-QTOF | splash10-0a4r-9000000000-a0b510d0bb7d05639321 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 10V, Negative-QTOF | splash10-014i-0900000000-cbb46b5675b53a8d8e5a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 20V, Negative-QTOF | splash10-014i-0900000000-9209faee800d5ed69a12 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 40V, Negative-QTOF | splash10-053r-9300000000-5a50b75ac1afd271f229 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 10V, Negative-QTOF | splash10-014i-0900000000-930f9ca2cc854ecca14e | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 20V, Negative-QTOF | splash10-014r-0900000000-5d00430d35645813b70d | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 40V, Negative-QTOF | splash10-0pb9-9000000000-f02aafeecdfdc9fdf127 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 10V, Positive-QTOF | splash10-014i-0900000000-c786d8eceea8c0b665cd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 20V, Positive-QTOF | splash10-05n0-7900000000-38659fd0669fff748e67 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Thermophillin 40V, Positive-QTOF | splash10-0a4l-9000000000-200fa817584bc784e56d | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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 | FDB012694 |
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KNApSAcK ID | C00036463 |
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Chemspider ID | 91630 |
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KEGG Compound ID | C01692 |
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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 | 101405 |
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PDB ID | Not Available |
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ChEBI ID | 4659 |
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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 | Not Available |
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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 | - Tomcik P, Krajcikova M, Bustin D: Determination of pharmaceutical dosage forms via diffusion layer titration at an interdigitated microelectrode array. Talanta. 2001 Dec 24;55(6):1065-70. [PubMed:18968458 ]
- Prancheva MG, Krasteva SA, Tufkova SG, Karaivanova TP, Nizamova VV, Iliev YT: Severe hypotension and ischemic stroke after disulfiram-ethanol reaction. Folia Med (Plovdiv). 2010 Jul-Sep;52(3):70-3. [PubMed:21053676 ]
- Haley TJ: Disulfiram (tetraethylthioperoxydicarbonic diamide): a reappraisal of its toxicity and therapeutic application. Drug Metab Rev. 1979;9(2):319-35. [PubMed:385275 ]
- Seino H, Yoshikawa T, Hidai M, Mizobe Y: Preparation of mononuclear and dinuclear Rh hydrotris(pyrazolyl)borato complexes containing arenethiolato ligands and conversion of the mononuclear complexes into dinuclear Rh-Rh and Rh-Ir complexes with bridging arenethiolato ligands. Dalton Trans. 2004 Nov 7;(21):3593-600. Epub 2004 Sep 29. [PubMed:15510281 ]
- Huang CJ, Li Y, Jiang S: Zwitterionic polymer-based platform with two-layer architecture for ultra low fouling and high protein loading. Anal Chem. 2012 Apr 3;84(7):3440-5. doi: 10.1021/ac3003769. Epub 2012 Mar 21. [PubMed:22409836 ]
- Kitano H, Kawasaki A, Kawasaki H, Morokoshi S: Resistance of zwitterionic telomers accumulated on metal surfaces against nonspecific adsorption of proteins. J Colloid Interface Sci. 2005 Feb 15;282(2):340-8. [PubMed:15589539 ]
- Driscoll WJ, Mueller SA, Eipper BA, Mueller GP: Differential regulation of peptide alpha-amidation by dexamethasone and disulfiram. Mol Pharmacol. 1999 Jun;55(6):1067-76. [PubMed:10347250 ]
- Bancos I, Bida JP, Tian D, Bundrick M, John K, Holte MN, Her YF, Evans D, Saenz DT, Poeschla EM, Hook D, Georg G, Maher LJ 3rd: High-throughput screening for growth inhibitors using a yeast model of familial paraganglioma. PLoS One. 2013;8(2):e56827. doi: 10.1371/journal.pone.0056827. Epub 2013 Feb 22. [PubMed:23451094 ]
- Cao YC, Wang J: One-pot synthesis of high-quality zinc-blende CdS nanocrystals. J Am Chem Soc. 2004 Nov 10;126(44):14336-7. [PubMed:15521736 ]
- Kitano H, Morokoshi S, Ohhori K, Gemmei-Ide M, Yokoyama Y, Ohno K: Accumulation of phenyl boronic acid-carrying telomers on a gold surface. J Colloid Interface Sci. 2004 May 1;273(1):106-14. [PubMed:15051439 ]
- Kaminski ZW, Jezewska MM: Involvement of a single thiol group in the conversion of the NAD+-dependent activity of rat liver xanthine oxidoreductase to the O2-dependent activity. Biochem J. 1982 Nov 1;207(2):341-6. [PubMed:6961918 ]
- Hu F, Dou W, Wang JJ, Jia FX, Wang JJ: Purification and biochemical characterization of glutathione S-transferases from four field populations of Bactrocera dorsalis (Hendel) (Diptera: Tephritidae). Arch Insect Biochem Physiol. 2011 Dec;78(4):201-15. doi: 10.1002/arch.20453. [PubMed:22105666 ]
- Kontani Y, Kawasaki S, Kaneko M, Matsuda K, Sakata SF, Tamaki N: Inhibitory effect of ethanol administration on beta-alanine-2-oxoglutarate aminotransferase (GABA aminotransferase) in disulfiram-pretreated rats. J Nutr Sci Vitaminol (Tokyo). 1998 Feb;44(1):165-76. [PubMed:9591243 ]
- BARTONICEK V, TEISINGER J: [EFFECT OF STOPETHYL (TETRAETHYLTHIURAM DISULFIDE) ON TRICHLOROETHYLENE METABOLISM IN MAN]. Prac Lek. 1963 Apr;15:105-8. [PubMed:14093250 ]
- Sorensen JA, Andersen O, Nielsen JB: An in vivo study of the gastrointestinal absorption site for zinc chloride in mice. J Trace Elem Med Biol. 1998 Mar;12(1):16-22. [PubMed:9638608 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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