Showing metabocard for methylselenol (MMDBc0047874)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:47:01 UTC
Update Date2024-04-30 20:31:49 UTC
Metabolite IDMMDBc0047874
Metabolite Identification
Common Namemethylselenol
DescriptionMethaneselenol, 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecb04c0ac8>


  Mrv0541 05161318242D          

  2  1  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Se  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecb04c0ac8>

HMDB0060488
     RDKit          3D
Methaneselenol
  6  5  0  0  0  0  0  0  0  0999 V2000
   -0.6021    0.0171   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.7455   -0.0650 Se  0  0  0  0  0  2  0  0  0  0  0  0
   -1.3016   -0.7151   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    0.1520    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    0.9712   -0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    0.3202    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
M  END
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3D SDF for #<Metabolite:0x00007fecb04c0ac8>


  Mrv0541 05161318242D          

  2  1  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Se  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047874

> <DATABASE_NAME>
MIME

> <SMILES>
C[SeH]

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

> <INCHI_KEY>
APKHDKJWSHYLEU-UHFFFAOYSA-N

> <FORMULA>
CH4Se

> <MOLECULAR_WEIGHT>
95.0

> <EXACT_MASS>
95.947821956

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
4.757287886859288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methaneselenol

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
0.06430000000000008

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
19.464000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methaneselenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fecb04c0ac8>

HMDB0060488
     RDKit          3D
Methaneselenol
  6  5  0  0  0  0  0  0  0  0999 V2000
   -0.6021    0.0171   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.7455   -0.0650 Se  0  0  0  0  0  2  0  0  0  0  0  0
   -1.3016   -0.7151   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    0.1520    1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    0.9712   -0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    0.3202    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
M  END
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PDB for #<Metabolite:0x00007fecb04c0ac8>

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2 Se   UNK     0       0.000   0.000   0.000  0.00  0.00          Se+0
CONECT    1    2                                                            
CONECT    2    1                                                            
MASTER        0    0    0    0    0    0    0    0    2    0    2    0
END
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3D PDB for #<Metabolite:0x00007fecb04c0ac8>

COMPND    HMDB0060488
HETATM    1  C1  UNL     1      -0.602   0.017  -0.008  1.00  0.00           C  
HETATM    2 SE1  UNL     1       1.165  -0.745  -0.065  1.00  0.00          SE  
HETATM    3  H1  UNL     1      -1.302  -0.715  -0.462  1.00  0.00           H  
HETATM    4  H2  UNL     1      -0.909   0.152   1.050  1.00  0.00           H  
HETATM    5  H3  UNL     1      -0.592   0.971  -0.563  1.00  0.00           H  
HETATM    6  H4  UNL     1       2.239   0.320   0.048  1.00  0.00           H  
CONECT    1    2    3    4    5
CONECT    2    6
END
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SMILES for #<Metabolite:0x00007fecb04c0ac8>

C[SeH]
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INCHI for #<Metabolite:0x00007fecb04c0ac8>

InChI=1S/CH4Se/c1-2/h2H,1H3
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Synonyms
ValueSource
MethylselenolKegg
MethaneselenolChEBI
Molecular FormulaCH4Se
Average Mass95.0
Monoisotopic Mass95.947821956
IUPAC Namemethaneselenol
Traditional Namemethaneselenol
CAS Registry NumberNot Available
SMILES
C[SeH]
InChI Identifier
InChI=1S/CH4Se/c1-2/h2H,1H3
InChI KeyAPKHDKJWSHYLEU-UHFFFAOYSA-N