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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:48:36 UTC

Update Date

2022-03-07 02:54:15 UTC

HMDB ID

HMDB0034878

Secondary Accession Numbers

HMDB34878

Metabolite Identification

Common Name

3-Mercapto-2-methylpentanol

Description

3-Mercapto-2-methylpentanol, also known as 2-methyl-3-sulphanylpentan-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. 3-Mercapto-2-methylpentanol is an onion and sulfurous tasting compound. 3-Mercapto-2-methylpentanol has been detected, but not quantified in, several different foods, such as green onion, garden onion (var.), onion-family vegetables, welsh onions (Allium fistulosum), and red onion. This could make 3-mercapto-2-methylpentanol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Mercapto-2-methylpentanol.

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-Mercapto-2-methylpentan-1-ol	HMDB
2-Methyl-3-sulphanylpentan-1-ol	HMDB

Chemical Formula

C₆H₁₄OS

Average Molecular Weight

134.24

Monoisotopic Molecular Weight

134.07653576

IUPAC Name

2-methyl-3-sulfanylpentan-1-ol

Traditional Name

2-methyl-3-sulfanylpentan-1-ol

CAS Registry Number

227456-27-1

SMILES

CCC(S)C(C)CO

InChI Identifier

InChI=1S/C6H14OS/c1-3-6(8)5(2)4-7/h5-8H,3-4H2,1-2H3

InChI Key

HABNNYNSJFKZFE-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

Cellular substructure

Extracellular (HMDB: HMDB0034878)
Cytoplasm (HMDB: HMDB0034878)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034878)

Source

Exogenous

Food

Food (HMDB: HMDB0034878)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Endogenous

Plant

Plant (HMDB: HMDB0034878)

Not Available

Nutrient (HMDB: HMDB0034878)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	50.00 °C. @ 0.50 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.626 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.36 g/L	ALOGPS
logP	2.17	ALOGPS
logP	1.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.02	ChemAxon
pKa (Strongest Basic)	-2.6	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	3	ChemAxon
Refractivity	38.86 m³·mol⁻¹	ChemAxon
Polarizability	15.6 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]+	128.89	31661259
DarkChem	[M-H]-	125.762	31661259
DeepCCS	[M+H]+	133.122	30932474
DeepCCS	[M-H]-	130.988	30932474
DeepCCS	[M-2H]-	166.872	30932474
DeepCCS	[M+Na]+	141.709	30932474
AllCCS	[M+H]+	131.8	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	139.7	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-2-methylpentanol	CCC(S)C(C)CO	1766.7	Standard polar	33892256
3-Mercapto-2-methylpentanol	CCC(S)C(C)CO	1064.1	Standard non polar	33892256
3-Mercapto-2-methylpentanol	CCC(S)C(C)CO	1110.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-2-methylpentanol,1TMS,isomer #1	CCC(S)C(C)CO[Si](C)(C)C	1191.4	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,1TMS,isomer #2	CCC(S[Si](C)(C)C)C(C)CO	1262.2	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,2TMS,isomer #1	CCC(S[Si](C)(C)C)C(C)CO[Si](C)(C)C	1356.8	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,2TMS,isomer #1	CCC(S[Si](C)(C)C)C(C)CO[Si](C)(C)C	1384.5	Standard non polar	33892256
3-Mercapto-2-methylpentanol,1TBDMS,isomer #1	CCC(S)C(C)CO[Si](C)(C)C(C)(C)C	1408.4	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,1TBDMS,isomer #2	CCC(S[Si](C)(C)C(C)(C)C)C(C)CO	1487.9	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,2TBDMS,isomer #1	CCC(S[Si](C)(C)C(C)(C)C)C(C)CO[Si](C)(C)C(C)(C)C	1776.2	Semi standard non polar	33892256
3-Mercapto-2-methylpentanol,2TBDMS,isomer #1	CCC(S[Si](C)(C)C(C)(C)C)C(C)CO[Si](C)(C)C(C)(C)C	1831.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-2-methylpentanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fc0-9400000000-6a96beee4e6925912cfc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-2-methylpentanol GC-MS (1 TMS) - 70eV, Positive	splash10-0fml-9700000000-182ee26d726f523c738b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-2-methylpentanol 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 - 3-Mercapto-2-methylpentanol 10V, Positive-QTOF	splash10-00kr-3900000000-bcf097663076a6d3cd57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 20V, Positive-QTOF	splash10-016r-9800000000-6306fce168909465c6f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 40V, Positive-QTOF	splash10-002f-9000000000-78b239d246d6dc9e3188	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 10V, Negative-QTOF	splash10-001j-9800000000-23885597b866fac9d03a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 20V, Negative-QTOF	splash10-00lr-9800000000-b7d576d27f3db74d0e0e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 40V, Negative-QTOF	splash10-053u-9100000000-1f041a051a070aada9ab	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 10V, Positive-QTOF	splash10-0uyi-9700000000-967c2da19c7272c1162e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 20V, Positive-QTOF	splash10-005c-9100000000-8d764e465efd2d1d830f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 40V, Positive-QTOF	splash10-002f-9100000000-2f5f5de87bae577bccdf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 10V, Negative-QTOF	splash10-001i-1900000000-1d46a0a5ee1d8caf4bf5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 20V, Negative-QTOF	splash10-001j-9500000000-0a86d224f87c365a96d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-2-methylpentanol 40V, Negative-QTOF	splash10-001i-9000000000-7e25bd9b3592f2f18788	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

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

FDB013453

KNApSAcK ID

Not Available

Chemspider ID

4936226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6430888

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1576741

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 3-Mercapto-2-methylpentanol (HMDB0034878)

MOL for HMDB0034878 (3-Mercapto-2-methylpentanol)

3D MOL for HMDB0034878 (3-Mercapto-2-methylpentanol)

3D SDF for HMDB0034878 (3-Mercapto-2-methylpentanol)

3D-SDF for HMDB0034878 (3-Mercapto-2-methylpentanol)

PDB for HMDB0034878 (3-Mercapto-2-methylpentanol)

3D PDB for HMDB0034878 (3-Mercapto-2-methylpentanol)

SMILES for HMDB0034878 (3-Mercapto-2-methylpentanol)

INCHI for HMDB0034878 (3-Mercapto-2-methylpentanol)

Structure for HMDB0034878 (3-Mercapto-2-methylpentanol)

3D Structure for HMDB0034878 (3-Mercapto-2-methylpentanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra