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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:19:17 UTC

Update Date

2023-02-21 17:27:07 UTC

HMDB ID

HMDB0039781

Secondary Accession Numbers

HMDB39781

Metabolite Identification

Common Name

xi-2-Mercapto-3-methyl-1-butanol

Description

xi-2-Mercapto-3-methyl-1-butanol, also known as 3-methyl-2-sulphanylbutan-1-ol, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. xi-2-Mercapto-3-methyl-1-butanol has been detected, but not quantified in, alcoholic beverages. This could make XI-2-mercapto-3-methyl-1-butanol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on xi-2-Mercapto-3-methyl-1-butanol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-2-sulphanylbutan-1-ol	HMDB

Chemical Formula

C₅H₁₂OS

Average Molecular Weight

120.213

Monoisotopic Molecular Weight

120.060885696

IUPAC Name

3-methyl-2-sulfanylbutan-1-ol

Traditional Name

3-methyl-2-sulfanylbutan-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)C(S)CO

InChI Identifier

InChI=1S/C5H12OS/c1-4(2)5(7)3-6/h4-7H,3H2,1-2H3

InChI Key

QBYYSQQYPUMFOX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiols

Sub Class

Alkylthiols

Direct Parent

Alkylthiols

Alternative Parents

Substituents

Alkylthiol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039781)
Cytoplasm (HMDB: HMDB0039781)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039781)

Source

Exogenous

Exogenous (HMDB: HMDB0039781)

Food

Food (HMDB: HMDB0039781)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039781)

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	4.98 g/L	ALOGPS
logP	1.44	ALOGPS
logP	1.17	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.12 m³·mol⁻¹	ChemAxon
Polarizability	13.77 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]+	124.696	31661259
DarkChem	[M-H]-	119.328	31661259
DeepCCS	[M+H]+	129.723	30932474
DeepCCS	[M-H]-	127.685	30932474
DeepCCS	[M-2H]-	163.316	30932474
DeepCCS	[M+Na]+	138.001	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	124.3	32859911
AllCCS	[M+NH4]+	132.2	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	138.0	32859911
AllCCS	[M+HCOO]-	142.4	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.	2.25 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5048 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1846.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	426.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	264.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	473.4 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	591.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	281.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	890.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	354.1 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	1239.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	509.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	416.8 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	80.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
xi-2-Mercapto-3-methyl-1-butanol	CC(C)C(S)CO	1678.9	Standard polar	33892256
xi-2-Mercapto-3-methyl-1-butanol	CC(C)C(S)CO	970.1	Standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol	CC(C)C(S)CO	1005.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
xi-2-Mercapto-3-methyl-1-butanol,1TMS,isomer #1	CC(C)C(S)CO[Si](C)(C)C	1111.2	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,1TMS,isomer #2	CC(C)C(CO)S[Si](C)(C)C	1131.8	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,2TMS,isomer #1	CC(C)C(CO[Si](C)(C)C)S[Si](C)(C)C	1276.1	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,2TMS,isomer #1	CC(C)C(CO[Si](C)(C)C)S[Si](C)(C)C	1276.6	Standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,1TBDMS,isomer #1	CC(C)C(S)CO[Si](C)(C)C(C)(C)C	1313.1	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,1TBDMS,isomer #2	CC(C)C(CO)S[Si](C)(C)C(C)(C)C	1368.6	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,2TBDMS,isomer #1	CC(C)C(CO[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1679.8	Semi standard non polar	33892256
xi-2-Mercapto-3-methyl-1-butanol,2TBDMS,isomer #1	CC(C)C(CO[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1714.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-9100000000-8d63244a1fe77d2a9f2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol GC-MS (1 TMS) - 70eV, Positive	splash10-00g3-9400000000-526853221fb0d8d812d8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 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 - xi-2-Mercapto-3-methyl-1-butanol 10V, Positive-QTOF	splash10-0fk9-4900000000-be1ea70bd47dda75b320	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 20V, Positive-QTOF	splash10-0fml-9500000000-e669760fb410d24ec24a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 40V, Positive-QTOF	splash10-014l-9100000000-af31280034b2d00a46e9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 10V, Negative-QTOF	splash10-014r-9800000000-4290a16f027caee092da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 20V, Negative-QTOF	splash10-052r-9100000000-40ea5a4be26d3e891bac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 40V, Negative-QTOF	splash10-0080-9000000000-4c8a1524c365adf40154	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 10V, Positive-QTOF	splash10-0udi-9700000000-4fd1956bc75afbe3f14d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 20V, Positive-QTOF	splash10-014i-9100000000-adc62aa0c74a928dee32	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 40V, Positive-QTOF	splash10-014l-9000000000-3ac4fc620a7c86e3007a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 10V, Negative-QTOF	splash10-014i-0900000000-81dd6dbb55b02d458192	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 20V, Negative-QTOF	splash10-015i-9500000000-96ca13deb756089bd60a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2-Mercapto-3-methyl-1-butanol 40V, Negative-QTOF	splash10-001i-9000000000-90533388ca08fdb29f4b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB019431

KNApSAcK ID

Not Available

Chemspider ID

14298727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14249191

PDB ID

Not Available

ChEBI ID

Not Available

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

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

Showing metabocard for xi-2-Mercapto-3-methyl-1-butanol (HMDB0039781)

MOL for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

3D MOL for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

3D SDF for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

3D-SDF for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

PDB for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

3D PDB for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

SMILES for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

INCHI for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

Structure for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

3D Structure for HMDB0039781 (xi-2-Mercapto-3-methyl-1-butanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra