| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2013-05-17 01:24:25 UTC |
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| Update Date | 2022-03-07 03:17:45 UTC |
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| HMDB ID | HMDB0060488 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Methaneselenol |
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| Description | Methaneselenol, commonly referred to as methylselenol, is an organoselenium compound that is a selenium analogue of methanol. It consists of a methyl group covalently bound to a selenol group. Methylselenol is a naturally produced metabolite of selenium (Se), an essential trace element (PMID: 25258323 ). Inorganic selenium is mainly represented by selenate and selenite, whereas the organic selenium forms are represented by the selenoamino acids: selenomethionine (SeMet), selenocysteine (SeCys) and selenium methylselenocysteine (MSC) (PMID: 25258323 ). SeMet and MSC can be found in vegetables such as garlic and onions. Selenite is reduced in the presence of glutathione to selenide (H2Se). SeMet and selenocysteine (SeCys2) are also primarily converted to selenide and incorporated into selenoproteins or selenosugars. On the other hand, MSC (a natural metabolite) and the antineoplastic drug methylselenic acid (MSA) are converted to methylselenol by the enzyme beta-lyase (PMID: 25258323 ). Both selenide and methylselenol are highly reactive and both can interconvert through methylation/demethylation activities. Methylselenol is thought to be most significant in the anticancer activity of Se compounds (PMID: 30241340 ). Redox active Se compounds such as methylselenol have gained significant attention in the past decade as potential cancer therapeutic agents. Methylselenol is known for its action to selectively kill transformed cells through mechanisms that include increased formation of reactive oxygen species, induction of DNA damage, triggering of apoptosis, and inhibition of angiogenesis. Methylselenol also regulates the expression of ligands that trigger immune activation through the lymphocyte receptor NKG2D. The expression of NKG2D ligands is induced by stress-associated pathways that occur early during malignant transformation and enable the recognition and elimination of tumors by activating the lymphocyte receptor NKG2D (PMID: 25258323 ). This suggests that the application of selenium compounds that are metabolized to CH3SeH could improve NKG2D-based immune therapy for cancer treatment. |
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| Structure | InChI=1S/CH4Se/c1-2/h2H,1H3 |
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| Synonyms | | Value | Source |
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| Methylselenol | Kegg | | Methaneselenol | ChEBI |
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| Chemical Formula | CH4Se |
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| Average Molecular Weight | 95.0 |
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| Monoisotopic Molecular Weight | 95.947821956 |
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| IUPAC Name | methaneselenol |
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| Traditional Name | methaneselenol |
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| CAS Registry Number | Not Available |
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| SMILES | C[SeH] |
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| InChI Identifier | InChI=1S/CH4Se/c1-2/h2H,1H3 |
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| InChI Key | APKHDKJWSHYLEU-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as selenols. These are organic compounds that contains the functional group with the connectivity R-Se-H. |
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| Kingdom | Organic compounds |
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| Super Class | Organometallic compounds |
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| Class | Organometalloid compounds |
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| Sub Class | Organoselenium compounds |
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| Direct Parent | Selenols |
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| Alternative Parents | |
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| Substituents | - Hydrocarbon derivative
- Selenol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Not Available | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1297.0 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 523.2 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 216.0 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 405.9 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 235.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 410.8 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 509.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 618.6 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 888.9 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 295.6 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 995.2 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 369.1 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 407.0 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 771.7 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 493.6 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 289.3 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatized |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - Methaneselenol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-9000000000-0ad8c1eee45c56fe8f2b | 2016-09-22 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Methaneselenol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 10V, Positive-QTOF | splash10-0002-9000000000-e4d95352b945b461c692 | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 20V, Positive-QTOF | splash10-0002-9000000000-e4d95352b945b461c692 | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 40V, Positive-QTOF | splash10-0002-9000000000-e4d95352b945b461c692 | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 10V, Negative-QTOF | splash10-0006-9000000000-714d406c305f53bf1f7b | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 20V, Negative-QTOF | splash10-0006-9000000000-714d406c305f53bf1f7b | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 40V, Negative-QTOF | splash10-0006-9000000000-714d406c305f53bf1f7b | 2016-09-14 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 10V, Positive-QTOF | splash10-0002-9000000000-186d833c2a1d3a4b8f2b | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 20V, Positive-QTOF | splash10-0002-9000000000-186d833c2a1d3a4b8f2b | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 40V, Positive-QTOF | splash10-0002-9000000000-186d833c2a1d3a4b8f2b | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 10V, Negative-QTOF | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 20V, Negative-QTOF | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methaneselenol 40V, Negative-QTOF | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | 2021-10-12 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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| General References | - Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
- Hagemann-Jensen M, Uhlenbrock F, Kehlet S, Andresen L, Gabel-Jensen C, Ellgaard L, Gammelgaard B, Skov S: The selenium metabolite methylselenol regulates the expression of ligands that trigger immune activation through the lymphocyte receptor NKG2D. J Biol Chem. 2014 Nov 7;289(45):31576-90. doi: 10.1074/jbc.M114.591537. Epub 2014 Sep 25. [PubMed:25258323 ]
- Khalkar P, Diaz-Argelich N, Antonio Palop J, Sanmartin C, Fernandes AP: Novel Methylselenoesters Induce Programed Cell Death via Entosis in Pancreatic Cancer Cells. Int J Mol Sci. 2018 Sep 20;19(10). pii: ijms19102849. doi: 10.3390/ijms19102849. [PubMed:30241340 ]
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