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Showing NP-Card for 4-methyl-4-sulfanylpentan-2-one (NP0163630)

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Record Information
Version2.0
Created at2022-09-02 22:19:39 UTC
Updated at2022-09-02 22:19:39 UTC
NP-MRD IDNP0163630
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-methyl-4-sulfanylpentan-2-one
Description4-Mercapto-4-methyl-2-pentanone, also known as 4-sulfanyl-4-methylpentan-2-one or 4-methyl-4-sulfanyl-2-pentanone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 4-mercapto-4-methyl-2-pentanone is considered to be an oxygenated hydrocarbon lipid molecule. An alkylthiol that is 4-methylpentan-2-one substituted at position 4 by a mercapto group. 4-Mercapto-4-methyl-2-pentanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Mercapto-4-methyl-2-pentanone is a blackcurrant, box tree, and cat-urine tasting compound. Outside of the human body, 4-Mercapto-4-methyl-2-pentanone has been detected, but not quantified in, alcoholic beverages. 4-methyl-4-sulfanylpentan-2-one is found in Cytisus scoparius, Humulus lupulus and Vitis vinifera. 4-methyl-4-sulfanylpentan-2-one was first documented in 2008 (PMID: 18173243). This could make 4-mercapto-4-methyl-2-pentanone a potential biomarker for the consumption of these foods (PMID: 19125618) (PMID: 20122692) (PMID: 21569935) (PMID: 24034138).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0163630 (4-methyl-4-sulfanylpentan-2-one)


  Mrv0541 05061305582D          

  8  7  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0163630 (4-methyl-4-sulfanylpentan-2-one)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
    2.7980   -0.2478    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    0.0083    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    0.4295    1.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4603   -0.2872   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9860   -0.0207   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666    1.4269    0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -0.8931    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -0.3852   -1.8735 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9080   -1.3531    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4098    0.2425    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891    0.1573   -0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7965    0.3480   -1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5874   -1.3394   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902    1.6448   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    2.1231   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    1.5610    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755   -0.3365    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -1.8144    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -1.1811    1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.0829   -2.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
M  END
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3D SDF for NP0163630 (4-methyl-4-sulfanylpentan-2-one)


  Mrv0541 05061305582D          

  8  7  0  0  0  0            999 V2000
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163630

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

> <INCHI_KEY>
QRNZMFDCKKEPSX-UHFFFAOYSA-N

> <FORMULA>
C6H12OS

> <MOLECULAR_WEIGHT>
132.224

> <EXACT_MASS>
132.060885696

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.608897402010452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-4-sulfanylpentan-2-one

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.2670096590000004

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.187992120103495

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.924465813766583

> <JCHEM_PKA_STRONGEST_BASIC>
-7.301481370682229

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
37.7804

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-4-sulfanylpentan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0163630 (4-methyl-4-sulfanylpentan-2-one)

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PDB for NP0163630 (4-methyl-4-sulfanylpentan-2-one)
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       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    5    6                                                       
CONECT    5    1    4    7                                                  
CONECT    6    2    3    4    8                                             
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0163630 (4-methyl-4-sulfanylpentan-2-one)
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SMILES for NP0163630 (4-methyl-4-sulfanylpentan-2-one)
CC(=O)CC(C)(C)S
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INCHI for NP0163630 (4-methyl-4-sulfanylpentan-2-one)
InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
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View in JSmol
Synonyms
ValueSource
4-Methyl-4-mercapto-2-pentanoneChEBI
4-Methyl-4-mercaptopentan-2-oneChEBI
4-Methyl-4-sulfanyl-2-pentanoneChEBI
4-Methyl-4-thiolpentan-2-oneChEBI
4-Sulfanyl-4-methylpentan-2-oneChEBI
4-Sulphanyl-4-methylpentan-2-oneChEBI
4-Methyl-4-sulphanyl-2-pentanoneGenerator
4-Mercapto-4-methyl-pentan-2-oneHMDB
4-Mercapto-4-methylpentan-2-oneHMDB
4-Methyl-4-mercapto-pentan-2-oneHMDB
4-Mercapto-4-methyl-2-pentanoneChEBI
Chemical FormulaC6H12OS
Average Mass132.2240 Da
Monoisotopic Mass132.06089 Da
IUPAC Name4-methyl-4-sulfanylpentan-2-one
Traditional Name4-methyl-4-sulfanylpentan-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)CC(C)(C)S
InChI Identifier
InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeyQRNZMFDCKKEPSX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cytisus scopariusLOTUS Database
Humulus lupulusLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentKetones  
Alternative Parents
Substituents
  • Ketone
    • 

  • Alkylthiol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP2.01ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.78 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031519  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008119  
KNApSAcK IDNot Available
Chemspider ID79650  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Mercapto-4-methyl-2-pentanone  
METLIN IDNot Available
PubChem Compound88290  
PDB IDNot Available
ChEBI ID77856  
Good Scents IDNot Available
References
General References
  1. Kishimoto T, Kobayashi M, Yako N, Iida A, Wanikawa A: Comparison of 4-Mercapto-4-methylpentan-2-one contents in hop cultivars from different growing regions. J Agric Food Chem. 2008 Feb 13;56(3):1051-7. doi: 10.1021/jf072173e. Epub 2008  Jan 4. [PubMed:18173243  ] 
  2. Fedrizzi B, Pardon KH, Sefton MA, Elsey GM, Jeffery DW: First identification of 4-S-glutathionyl-4-methylpentan-2-one, a potential precursor of 4-mercapto-4-methylpentan-2-one, in Sauvignon Blanc juice. J Agric Food Chem. 2009 Feb 11;57(3):991-5. doi: 10.1021/jf802799w. [PubMed:19125618  ] 
  3. Roland A, Vialaret J, Moniatte M, Rigou P, Razungles A, Schneider R: Validation of a nanoliquid chromatography-tandem mass spectrometry method for the identification and the accurate quantification by isotopic dilution of glutathionylated and cysteinylated precursors of 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one in white grape juices. J Chromatogr A. 2010 Mar 5;1217(10):1626-35. doi: 10.1016/j.chroma.2010.01.031.  Epub 2010 Jan 18. [PubMed:20122692  ] 
  4. Roncoroni M, Santiago M, Hooks DO, Moroney S, Harsch MJ, Lee SA, Richards KD, Nicolau L, Gardner RC: The yeast IRC7 gene encodes a beta-lyase responsible for production of the varietal thiol 4-mercapto-4-methylpentan-2-one in wine. Food Microbiol. 2011 Aug;28(5):926-35. doi: 10.1016/j.fm.2011.01.002. Epub 2011  Jan 13. [PubMed:21569935  ] 
  5. Herbst-Johnstone M, Piano F, Duhamel N, Barker D, Fedrizzi B: Ethyl propiolate derivatisation for the analysis of varietal thiols in wine. J Chromatogr A. 2013 Oct 18;1312:104-10. doi: 10.1016/j.chroma.2013.08.066. Epub  2013 Aug 26. [PubMed:24034138  ] 
  6. LOTUS database [Link]