| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-26 00:25:38 UTC |
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| Update Date | 2016-11-09 01:18:41 UTC |
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| Accession Number | CHEM028393 |
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| Identification |
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| Common Name | Physalin L |
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| Class | Small Molecule |
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| Description | 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 tolerance. Thermophillin is found in herbs and spices and root vegetables. |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 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 | | 2,5-Dimethoxy-4-benzoquinone | HMDB | | Physalin L | MeSH |
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| Chemical Formula | C28H32O10 |
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| Average Molecular Mass | 528.548 g/mol |
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| Monoisotopic Mass | 528.200 g/mol |
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| CAS Registry Number | 113146-74-0 |
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| IUPAC Name | 5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone |
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| Traditional Name | 5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone |
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| SMILES | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC11C2(C)OC(=O)C1(O)CCC1C3C(O)C=C2C=CCC(=O)C12C |
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| InChI Identifier | InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5-6,10,12,14-15,17-19,29,34-35H,7-9,11H2,1-4H3 |
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| InChI Key | CUSXWWXXAPEFHY-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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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0uea-0941530000-873f1663fd91ebacf479 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0pdi-2920008000-963f7adf833516fbbb12 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_9) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03fr-0000490000-e62e78921c0e9a535e12 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-0000950000-9c67dbd40be87bc29469 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05mo-0000900000-21e169791d2ee393ba1b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000590000-daea3f0810eecd620016 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-0000690000-1cec3bc936abc6574583 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-1970410000-9b8b36c7c8525e26c312 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000090000-a4d87ed97fdb1a342963 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0100790000-3b4a5c3b90f86dc3037a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fmi-0900120000-8c46e2c8660008723b8a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000190000-dc66cc185ead90926e8f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000190000-d193e36b8da7150fb2be | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-0540790000-f6d76f37a22612b81caf | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0034335 |
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| FooDB ID | FDB012694 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 91630 |
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| ChEBI ID | 4659 |
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| PubChem Compound ID | 101405 |
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| Kegg Compound ID | C01692 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. 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. | | 2. Haley TJ: Disulfiram (tetraethylthioperoxydicarbonic diamide): a reappraisal of its toxicity and therapeutic application. Drug Metab Rev. 1979;9(2):319-35. | | 3. 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. | | 4. 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. | | 5. 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. | | 6. 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. | | 7. 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. | | 8. 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. | | 9. 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. | | 10. 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. | | 11. 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. | | 12. 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. | | 13. 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. | | 14. BARTONICEK V, TEISINGER J: [EFFECT OF STOPETHYL (TETRAETHYLTHIURAM DISULFIDE) ON TRICHLOROETHYLENE METABOLISM IN MAN]. Prac Lek. 1963 Apr;15:105-8. | | 15. 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. | | 16. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. |
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