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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:24:25 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060488

Secondary Accession Numbers

HMDB60488

Metabolite Identification

Common Name

Methaneselenol

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methylselenol	Kegg
Methaneselenol	ChEBI

Chemical Formula

CH₄Se

Average Molecular Weight

95.0

Monoisotopic Molecular Weight

95.947821956

IUPAC Name

methaneselenol

Traditional Name

methaneselenol

CAS Registry Number

Not Available

SMILES

C[SeH]

InChI Identifier

InChI=1S/CH4Se/c1-2/h2H,1H3

InChI Key

APKHDKJWSHYLEU-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organoselenium compounds

Direct Parent

Selenols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Selenol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:64685 )
organoselenium compound (CHEBI:64685 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060488)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Selenocompound Metabolism (PathBank: SMP0002371)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	126 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	0.064	ChemAxon
logS	0.12	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	19.46 m³·mol⁻¹	ChemAxon
Polarizability	4.76 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	119.72	30932474
DeepCCS	[M-H]-	117.874	30932474
DeepCCS	[M-2H]-	153.189	30932474
DeepCCS	[M+Na]+	127.056	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	274.1	32859911
AllCCS	[M+Na-2H]-	284.7	32859911
AllCCS	[M+HCOO]-	296.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methaneselenol	C[SeH]	822.5	Standard polar	33892256
Methaneselenol	C[SeH]	411.9	Standard non polar	33892256
Methaneselenol	C[SeH]	540.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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
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
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBMET01461

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05703

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Selenol

METLIN ID

Not Available

PubChem Compound

440764

PDB ID

Not Available

ChEBI ID

64685

Food Biomarker Ontology

Not Available

VMH ID

M02469

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Enzymes

Enzyme Details

1. Thioredoxin reductase 1, cytoplasmic

General function:: Involved in oxidoreductase activity
Specific function:: Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enhances the transcriptional activity of estrogen receptors alpha and beta while isoform 5 enhances the transcriptional activity of the beta receptor only. Isoform 5 also mediates cell death induced by a combination of interferon-beta and retinoic acid.
Gene Name:: TXNRD1
Uniprot ID:: Q16881
Molecular weight:: 70905.58

Reactions

NADPH + Hydrogen Ion + Methylselenic acid → NADP + Water + Methaneselenol	details

Enzyme Details

2. Thioredoxin reductase 2, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Maintains thioredoxin in a reduced state. Implicated in the defenses against oxidative stress. May play a role in redox-regulated cell signaling.
Gene Name:: TXNRD2
Uniprot ID:: Q9NNW7
Molecular weight:: 56506.275

Reactions

NADPH + Hydrogen Ion + Methylselenic acid → NADP + Water + Methaneselenol	details

Enzyme Details

3. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Reactions

Selenomethionine + Water → Methaneselenol + Ammonia + 2-Ketobutyric acid	details

Enzyme Details

4. Selenocysteine lyase

General function:: Involved in metabolic process
Specific function:: Catalyzes the decomposition of L-selenocysteine to L-alanine and elemental selenium (By similarity).
Gene Name:: SCLY
Uniprot ID:: Q96I15
Molecular weight:: 48793.15

Reactions

Se-Methylselenocysteine + Water → Pyruvic acid + Ammonia + Methaneselenol	details

Enzyme Details

5. Thioredoxin reductase 3

General function:: Involved in oxidoreductase activity
Specific function:: Displays thioredoxin reductase, glutaredoxin and glutathione reductase activities. Catalyzes disulfide bond isomerization. Promotes disulfide bond formation between GPX4 and various sperm proteins and may play a role in sperm maturation by promoting formation of sperm structural components (By similarity).
Gene Name:: TXNRD3
Uniprot ID:: Q86VQ6
Molecular weight:: 66600.92

Reactions

NADPH + Hydrogen Ion + Methylselenic acid → NADP + Water + Methaneselenol	details

Showing metabocard for Methaneselenol (HMDB0060488)

MOL for HMDB0060488 (Methaneselenol)

3D MOL for HMDB0060488 (Methaneselenol)

3D SDF for HMDB0060488 (Methaneselenol)

3D-SDF for HMDB0060488 (Methaneselenol)

PDB for HMDB0060488 (Methaneselenol)

3D PDB for HMDB0060488 (Methaneselenol)

SMILES for HMDB0060488 (Methaneselenol)

INCHI for HMDB0060488 (Methaneselenol)

Structure for HMDB0060488 (Methaneselenol)

3D Structure for HMDB0060488 (Methaneselenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions