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Showing NP-Card for S-Methyl 3-methylthiobutyrate (NP0337742)

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Record Information
Version2.0
Created at2024-09-11 12:10:59 UTC
Updated at2024-09-11 12:10:59 UTC
NP-MRD IDNP0337742
Secondary Accession NumbersNone
Natural Product Identification
Common NameS-Methyl 3-methylthiobutyrate
DescriptionS-Methyl 3-methylthiobutyrate, also known as fema 3864 or methanethiol isovalerate, belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain. S-Methyl 3-methylthiobutyrate is an extremely weak basic (essentially neutral) compound (based on its pKa). S-Methyl 3-methylthiobutyrate is an acrid, cheese, and fermented tasting compound. Outside of the human body, S-Methyl 3-methylthiobutyrate has been detected, but not quantified in, fruits and milk and milk products. It was first documented in 2000 (PMID: 11413487). This could make S-methyl 3-methylthiobutyrate a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337742 (S-Methyl 3-methylthiobutyrate)


  Mrv0541 05061311262D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0337742 (S-Methyl 3-methylthiobutyrate)

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3D SDF for NP0337742 (S-Methyl 3-methylthiobutyrate)

  Mrv0541 05061311262D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC(=O)CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C6H12OS/c1-5(2)4-6(7)8-3/h5H,4H2,1-3H3

> <INCHI_KEY>
MPLWTJZAFOVXKP-UHFFFAOYSA-N

> <FORMULA>
C6H12OS

> <MOLECULAR_WEIGHT>
132.224

> <EXACT_MASS>
132.060885696

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.94591201906679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-1-(methylsulfanyl)butan-1-one

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
2.109301457

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.046044382822029

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
37.485

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-1-(methylsulfanyl)butan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337742 (S-Methyl 3-methylthiobutyrate)
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PDB for NP0337742 (S-Methyl 3-methylthiobutyrate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   3.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    8                                                            
CONECT    4    5    6                                                       
CONECT    5    1    2    4                                                  
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    3    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0337742 (S-Methyl 3-methylthiobutyrate)
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SMILES for NP0337742 (S-Methyl 3-methylthiobutyrate)
CSC(=O)CC(C)C
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INCHI for NP0337742 (S-Methyl 3-methylthiobutyrate)
InChI=1S/C6H12OS/c1-5(2)4-6(7)8-3/h5H,4H2,1-3H3
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Synonyms
ValueSource
S-Methyl 3-methylthiobutyric acidGenerator
Butanethioic acid, 3-methyl-, S-methyl esterHMDB
FEMA 3864HMDB
Methanethiol isovalerateHMDB
S-Methyl thio-3-methylbutyrateHMDB
S-Methyl thioisovalerateHMDB
3-Methyl-1-(methylsulphanyl)butan-1-oneGenerator
Chemical FormulaC6H12OS
Average Mass132.2240 Da
Monoisotopic Mass132.06089 Da
IUPAC Name3-methyl-1-(methylsulfanyl)butan-1-one
Traditional Name3-methyl-1-(methylsulfanyl)butan-1-one
CAS Registry NumberNot Available
SMILES
CSC(=O)CC(C)C
InChI Identifier
InChI=1S/C6H12OS/c1-5(2)4-6(7)8-3/h5H,4H2,1-3H3
InChI KeyMPLWTJZAFOVXKP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl thioesters  
Direct ParentFatty acyl thioesters  
Alternative Parents
Substituents
  • Fatty acyl thioester
    • 

  • Carbothioic s-ester
    • 

  • Thiocarboxylic acid ester
    • 

  • Sulfenyl compound
    • 

  • Thiocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.71ALOGPS
logP2.11ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.48 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039843  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019497  
KNApSAcK IDNot Available
Chemspider ID81472  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90246  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]