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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:28 UTC

Update Date

2023-02-21 17:21:59 UTC

HMDB ID

HMDB0032376

Secondary Accession Numbers

HMDB32376

Metabolite Identification

Common Name

4-Mercapto-2-pentanone

Description

4-Mercapto-2-pentanone, also known as 4-mercaptopentan-2-ol or 4-sulphanylpentan-2-one, 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. Based on a literature review very few articles have been published on 4-Mercapto-2-pentanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(p-Carboxyphenyl)(purin-6-ylthio)-mercury	HMDB
4-Mercaptopentan-2-ol	HMDB
4-Mercaptopentan-2-one	HMDB
p-[(Purin-6-ylthio)mercuri]-benzoic acid	HMDB
4-Sulphanylpentan-2-one	HMDB

Chemical Formula

C₅H₁₀OS

Average Molecular Weight

118.197

Monoisotopic Molecular Weight

118.045235632

IUPAC Name

4-sulfanylpentan-2-one

Traditional Name

4-sulfanylpentan-2-one

CAS Registry Number

92585-08-5

SMILES

CC(S)CC(C)=O

InChI Identifier

InChI=1S/C5H10OS/c1-4(6)3-5(2)7/h5,7H,3H2,1-2H3

InChI Key

KHIPEWLRUGVKIC-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

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Pungent

Odor

Meaty

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032376)
Cytoplasm (HMDB: HMDB0032376)

Source

Endogenous

Endogenous (HMDB: HMDB0032376)

Exogenous

Food

Food (HMDB: HMDB0032376)

Exogenous (HMDB: HMDB0032376)

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	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	3.75 g/L	ALOGPS
logP	1.68	ALOGPS
logP	1.09	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.03	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	33.09 m³·mol⁻¹	ChemAxon
Polarizability	12.9 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]+	124.292	31661259
DarkChem	[M-H]-	120.508	31661259
DeepCCS	[M+H]+	132.944	30932474
DeepCCS	[M-H]-	130.996	30932474
DeepCCS	[M-2H]-	166.857	30932474
DeepCCS	[M+Na]+	141.48	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.6	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	136.9	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.21 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5311 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1843.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	462.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	300.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	446.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	556.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	265.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	952.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	324.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1107.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	448.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	86.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Mercapto-2-pentanone	CC(S)CC(C)=O	1465.5	Standard polar	33892256
4-Mercapto-2-pentanone	CC(S)CC(C)=O	871.8	Standard non polar	33892256
4-Mercapto-2-pentanone	CC(S)CC(C)=O	901.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Mercapto-2-pentanone,1TMS,isomer #1	CC(=O)CC(C)S[Si](C)(C)C	1136.6	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TMS,isomer #1	CC(=O)CC(C)S[Si](C)(C)C	1128.6	Standard non polar	33892256
4-Mercapto-2-pentanone,1TMS,isomer #2	CC(=CC(C)S)O[Si](C)(C)C	1091.7	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TMS,isomer #2	CC(=CC(C)S)O[Si](C)(C)C	1166.0	Standard non polar	33892256
4-Mercapto-2-pentanone,1TMS,isomer #3	C=C(CC(C)S)O[Si](C)(C)C	1098.7	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TMS,isomer #3	C=C(CC(C)S)O[Si](C)(C)C	1133.5	Standard non polar	33892256
4-Mercapto-2-pentanone,2TMS,isomer #1	CC(=CC(C)S[Si](C)(C)C)O[Si](C)(C)C	1345.8	Semi standard non polar	33892256
4-Mercapto-2-pentanone,2TMS,isomer #1	CC(=CC(C)S[Si](C)(C)C)O[Si](C)(C)C	1346.2	Standard non polar	33892256
4-Mercapto-2-pentanone,2TMS,isomer #2	C=C(CC(C)S[Si](C)(C)C)O[Si](C)(C)C	1311.5	Semi standard non polar	33892256
4-Mercapto-2-pentanone,2TMS,isomer #2	C=C(CC(C)S[Si](C)(C)C)O[Si](C)(C)C	1371.2	Standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #1	CC(=O)CC(C)S[Si](C)(C)C(C)(C)C	1369.9	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #1	CC(=O)CC(C)S[Si](C)(C)C(C)(C)C	1373.2	Standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #2	CC(=CC(C)S)O[Si](C)(C)C(C)(C)C	1327.7	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #2	CC(=CC(C)S)O[Si](C)(C)C(C)(C)C	1393.4	Standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #3	C=C(CC(C)S)O[Si](C)(C)C(C)(C)C	1334.0	Semi standard non polar	33892256
4-Mercapto-2-pentanone,1TBDMS,isomer #3	C=C(CC(C)S)O[Si](C)(C)C(C)(C)C	1338.5	Standard non polar	33892256
4-Mercapto-2-pentanone,2TBDMS,isomer #1	CC(=CC(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1795.6	Semi standard non polar	33892256
4-Mercapto-2-pentanone,2TBDMS,isomer #1	CC(=CC(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1801.2	Standard non polar	33892256
4-Mercapto-2-pentanone,2TBDMS,isomer #2	C=C(CC(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1756.8	Semi standard non polar	33892256
4-Mercapto-2-pentanone,2TBDMS,isomer #2	C=C(CC(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1802.2	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-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-67ee89a4af9eaf0b5323	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Mercapto-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-2-pentanone 10V, Positive-QTOF	splash10-0gb9-4900000000-31b2aa9e4a0db0903879	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 20V, Positive-QTOF	splash10-0gb9-6900000000-3f0a95a335476fd96168	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 40V, Positive-QTOF	splash10-014l-9000000000-713adb305891ca46960d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 10V, Negative-QTOF	splash10-0159-8900000000-b2e32ea2da838e8443a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 20V, Negative-QTOF	splash10-0159-9500000000-7d73a5e46e4919ef518f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 40V, Negative-QTOF	splash10-001i-9000000000-7682c50bfc764abc8c51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 10V, Negative-QTOF	splash10-001i-9200000000-f4d68ecec3d159e1ee51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 20V, Negative-QTOF	splash10-00lr-9300000000-a75a1e24bbcde40aea44	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 40V, Negative-QTOF	splash10-0a59-9000000000-b33d6a904dfd5862ff28	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 10V, Positive-QTOF	splash10-03y0-9200000000-95c892677ef2792b1fde	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 20V, Positive-QTOF	splash10-01ox-9000000000-da3e67613a885545cb4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Mercapto-2-pentanone 40V, Positive-QTOF	splash10-0006-9000000000-5934ca1212c814f8953f	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, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB009793

KNApSAcK ID

Not Available

Chemspider ID

459655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

527393

PDB ID

Not Available

ChEBI ID

173441

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for 4-Mercapto-2-pentanone (HMDB0032376)

MOL for HMDB0032376 (4-Mercapto-2-pentanone)

3D MOL for HMDB0032376 (4-Mercapto-2-pentanone)

3D SDF for HMDB0032376 (4-Mercapto-2-pentanone)

3D-SDF for HMDB0032376 (4-Mercapto-2-pentanone)

PDB for HMDB0032376 (4-Mercapto-2-pentanone)

3D PDB for HMDB0032376 (4-Mercapto-2-pentanone)

SMILES for HMDB0032376 (4-Mercapto-2-pentanone)

INCHI for HMDB0032376 (4-Mercapto-2-pentanone)

Structure for HMDB0032376 (4-Mercapto-2-pentanone)

3D Structure for HMDB0032376 (4-Mercapto-2-pentanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra