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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:48 UTC

Update Date

2023-02-21 17:20:44 UTC

HMDB ID

HMDB0031519

Secondary Accession Numbers

HMDB31519

Metabolite Identification

Common Name

4-Mercapto-4-methyl-2-pentanone

Description

4-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. 4-Mercapto-4-methyl-2-pentanone is a blackcurrant, box tree, and cat-urine tasting compound. 4-Mercapto-4-methyl-2-pentanone has been detected, but not quantified in, alcoholic beverages and grape wine. This could make 4-mercapto-4-methyl-2-pentanone a potential biomarker for the consumption of these foods. 4-Mercapto-4-methyl-2-pentanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Mercapto-4-methyl-2-pentanone.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methyl-4-mercapto-2-pentanone	ChEBI
4-Methyl-4-mercaptopentan-2-one	ChEBI
4-Methyl-4-sulfanyl-2-pentanone	ChEBI
4-Methyl-4-thiolpentan-2-one	ChEBI
4-Sulfanyl-4-methylpentan-2-one	ChEBI
4-Sulphanyl-4-methylpentan-2-one	ChEBI
4-Methyl-4-sulphanyl-2-pentanone	Generator
4-mercapto-4-Methyl-pentan-2-one	HMDB
4-mercapto-4-Methylpentan-2-one	HMDB
4-Methyl-4-mercapto-pentan-2-one	HMDB
4-Mercapto-4-methyl-2-pentanone	ChEBI

Chemical Formula

C₆H₁₂OS

Average Molecular Weight

132.224

Monoisotopic Molecular Weight

132.060885696

IUPAC Name

4-methyl-4-sulfanylpentan-2-one

Traditional Name

4-methyl-4-sulfanylpentan-2-one

CAS Registry Number

19872-52-7

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

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Alkylthiol
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alkanethiol (CHEBI:77856 )
methyl ketone (CHEBI:77856 )
Oxygenated hydrocarbons (LMFA12000335 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031519)
Cytoplasm (HMDB: HMDB0031519)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031519)

Source

Endogenous

Endogenous (HMDB: HMDB0031519)

Exogenous

Food

Food (HMDB: HMDB0031519)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	181.65 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10970 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.432 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.78 m³·mol⁻¹	ChemAxon
Polarizability	14.61 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
DarkChem	[M+H]+	129.188	31661259
DarkChem	[M-H]-	124.024	31661259
DeepCCS	[M+H]+	133.705	30932474
DeepCCS	[M-H]-	131.256	30932474
DeepCCS	[M-2H]-	167.187	30932474
DeepCCS	[M+Na]+	142.415	30932474
AllCCS	[M+H]+	127.0	32859911
AllCCS	[M+H-H2O]+	122.9	32859911
AllCCS	[M+NH4]+	130.8	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	136.2	32859911
AllCCS	[M+HCOO]-	140.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Mercapto-4-methyl-2-pentanone	CC(=O)CC(C)(C)S	1437.8	Standard polar	33892256
4-Mercapto-4-methyl-2-pentanone	CC(=O)CC(C)(C)S	934.4	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone	CC(=O)CC(C)(C)S	942.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #1	CC(=O)CC(C)(C)S[Si](C)(C)C	1168.6	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #1	CC(=O)CC(C)(C)S[Si](C)(C)C	1198.1	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #2	CC(=CC(C)(C)S)O[Si](C)(C)C	1123.4	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #2	CC(=CC(C)(C)S)O[Si](C)(C)C	1212.0	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #3	C=C(CC(C)(C)S)O[Si](C)(C)C	1139.4	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #3	C=C(CC(C)(C)S)O[Si](C)(C)C	1178.7	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #1	CC(=CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1337.8	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #1	CC(=CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1391.3	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #2	C=C(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1356.1	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #2	C=C(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1409.9	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #1	CC(=O)CC(C)(C)S[Si](C)(C)C(C)(C)C	1410.7	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #1	CC(=O)CC(C)(C)S[Si](C)(C)C(C)(C)C	1435.2	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #2	CC(=CC(C)(C)S)O[Si](C)(C)C(C)(C)C	1332.6	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #2	CC(=CC(C)(C)S)O[Si](C)(C)C(C)(C)C	1433.2	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #3	C=C(CC(C)(C)S)O[Si](C)(C)C(C)(C)C	1357.8	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #3	C=C(CC(C)(C)S)O[Si](C)(C)C(C)(C)C	1378.2	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #1	CC(=CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1825.9	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #1	CC(=CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1843.5	Standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #2	C=C(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1829.4	Semi standard non polar	33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #2	C=C(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1836.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Mercapto-4-methyl-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9100000000-8e9ff8d3dd57a941e176	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 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 - 4-Mercapto-4-methyl-2-pentanone 10V, Positive-QTOF	splash10-00lr-3900000000-f7c166c594ab2f5bd9e6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Positive-QTOF	splash10-00lr-7900000000-415b660e2464f89dc70e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Positive-QTOF	splash10-001i-9100000000-cf87bb56a906d8284051	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Negative-QTOF	splash10-001j-7900000000-67facb7cefc788001bd4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Negative-QTOF	splash10-001j-9600000000-5a2f4ae474d4a47b0beb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Negative-QTOF	splash10-001i-9100000000-7653612fbae5886b1570	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Negative-QTOF	splash10-0002-9100000000-5b554632046f18361f55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Negative-QTOF	splash10-0089-9000000000-e5eeba93e8d05760b98b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Positive-QTOF	splash10-004m-9000000000-3a7dea1da5a4cd927037	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Positive-QTOF	splash10-004l-9000000000-99d12173b922c0f09a40	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Positive-QTOF	splash10-002f-9000000000-53764c8f862c3e9527d9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008119

KNApSAcK ID

Not Available

Chemspider ID

79650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Mercapto-4-methyl-2-pentanone

METLIN ID

Not Available

PubChem Compound

88290

PDB ID

Not Available

ChEBI ID

77856

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1038251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Mercapto-4-methyl-2-pentanone (HMDB0031519)

MOL for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

3D MOL for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

3D SDF for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

3D-SDF for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

PDB for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

3D PDB for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

SMILES for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

INCHI for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

Structure for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

3D Structure for HMDB0031519 (4-Mercapto-4-methyl-2-pentanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra