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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:41:48 UTC

Update Date

2023-02-21 17:27:46 UTC

HMDB ID

HMDB0040152

Secondary Accession Numbers

HMDB40152

Metabolite Identification

Common Name

3-Mercapto-1-hexanol

Description

3-Mercapto-1-hexanol, also known as 3-sulfanyl-1-hexanol, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. Thus, 3-mercapto-1-hexanol is considered to be a fatty alcohol. 3-Mercapto-1-hexanol is a sulfur tasting compound. 3-Mercapto-1-hexanol has been detected, but not quantified in, fruits. This could make 3-mercapto-1-hexanol a potential biomarker for the consumption of these foods. 3-Mercapto-1-hexanol 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 3-Mercapto-1-hexanol.

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-Mercaptohexan-1-ol	ChEBI
3-Sulfanyl-1-hexanol	ChEBI
3-Sulphanylhexan-1-ol	ChEBI
3-Sulphanyl-1-hexanol	Generator
3-Sulfanylhexan-1-ol	Generator
3-mercapto Hexan-1-ol	HMDB
3-Mercaptohexanol	HMDB
FEMA 3850	HMDB
3-Mercapto-1-hexanol	ChEBI

Chemical Formula

C₆H₁₄OS

Average Molecular Weight

134.24

Monoisotopic Molecular Weight

134.07653576

IUPAC Name

3-sulfanylhexan-1-ol

Traditional Name

3-sulfanylhexan-1-ol

CAS Registry Number

51755-83-0

SMILES

CCCC(S)CCO

InChI Identifier

InChI=1S/C6H14OS/c1-2-3-6(8)4-5-7/h6-8H,2-5H2,1H3

InChI Key

TYZFMFVWHZKYSE-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

primary alcohol (CHEBI:77690 )
alkanethiol (CHEBI:77690 )
Fatty alcohols (LMFA05000539 )

Ontology

Physiological effect

Organoleptic effect

Odor

Sulfur

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040152)
Cytoplasm (HMDB: HMDB0040152)

Source

Exogenous

Exogenous (HMDB: HMDB0040152)

Food

Fruit

Fruits (FooDB: FOOD00871)

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	198.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3166 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.644 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.4 g/L	ALOGPS
logP	2.06	ALOGPS
logP	1.38	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-2.4	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	4	ChemAxon
Refractivity	39.04 m³·mol⁻¹	ChemAxon
Polarizability	15.96 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]+	128.12	31661259
DarkChem	[M-H]-	124.643	31661259
DeepCCS	[M+H]+	132.907	30932474
DeepCCS	[M-H]-	130.023	30932474
DeepCCS	[M-2H]-	166.475	30932474
DeepCCS	[M+Na]+	141.354	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	128.0	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	144.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-1-hexanol	CCCC(S)CCO	1884.7	Standard polar	33892256
3-Mercapto-1-hexanol	CCCC(S)CCO	1092.2	Standard non polar	33892256
3-Mercapto-1-hexanol	CCCC(S)CCO	1154.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-1-hexanol,1TMS,isomer #1	CCCC(S)CCO[Si](C)(C)C	1255.0	Semi standard non polar	33892256
3-Mercapto-1-hexanol,1TMS,isomer #2	CCCC(CCO)S[Si](C)(C)C	1291.3	Semi standard non polar	33892256
3-Mercapto-1-hexanol,2TMS,isomer #1	CCCC(CCO[Si](C)(C)C)S[Si](C)(C)C	1400.7	Semi standard non polar	33892256
3-Mercapto-1-hexanol,2TMS,isomer #1	CCCC(CCO[Si](C)(C)C)S[Si](C)(C)C	1438.1	Standard non polar	33892256
3-Mercapto-1-hexanol,1TBDMS,isomer #1	CCCC(S)CCO[Si](C)(C)C(C)(C)C	1494.6	Semi standard non polar	33892256
3-Mercapto-1-hexanol,1TBDMS,isomer #2	CCCC(CCO)S[Si](C)(C)C(C)(C)C	1513.1	Semi standard non polar	33892256
3-Mercapto-1-hexanol,2TBDMS,isomer #1	CCCC(CCO[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1851.9	Semi standard non polar	33892256
3-Mercapto-1-hexanol,2TBDMS,isomer #1	CCCC(CCO[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1837.1	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-1-hexanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-9300000000-cb47450ccef913034114	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-1-hexanol GC-MS (1 TMS) - 70eV, Positive	splash10-0fmu-9600000000-4f2485ccfee0fa395205	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-1-hexanol 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-1-hexanol 10V, Positive-QTOF	splash10-00kr-2900000000-2024fed6b30387e6e269	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 20V, Positive-QTOF	splash10-014r-8900000000-c18323617e3c7b6ad0dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 40V, Positive-QTOF	splash10-0017-9000000000-f6688132bab19c0fa1ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 10V, Negative-QTOF	splash10-001j-9700000000-62e62f902b2b7e3a56bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 20V, Negative-QTOF	splash10-00lr-9800000000-d7cbbd5778886af450cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 40V, Negative-QTOF	splash10-001m-9000000000-6931c9af55ba327655cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 10V, Positive-QTOF	splash10-0gbi-7900000000-2afdbc2b3cc9185f0e72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 20V, Positive-QTOF	splash10-0a4i-9000000000-c36e45836a66e5a1f654	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 40V, Positive-QTOF	splash10-052f-9000000000-28802f08439ce171a674	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 10V, Negative-QTOF	splash10-001r-9800000000-16b165ad3a54528b0ffa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 20V, Negative-QTOF	splash10-001i-9000000000-4239a61f4e8d126c468f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-1-hexanol 40V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	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

FDB019857

KNApSAcK ID

C00052698

Chemspider ID

454763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

521348

PDB ID

Not Available

ChEBI ID

77690

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1102211

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-1-hexanol (HMDB0040152)

MOL for HMDB0040152 (3-Mercapto-1-hexanol)

3D MOL for HMDB0040152 (3-Mercapto-1-hexanol)

3D SDF for HMDB0040152 (3-Mercapto-1-hexanol)

3D-SDF for HMDB0040152 (3-Mercapto-1-hexanol)

PDB for HMDB0040152 (3-Mercapto-1-hexanol)

3D PDB for HMDB0040152 (3-Mercapto-1-hexanol)

SMILES for HMDB0040152 (3-Mercapto-1-hexanol)

INCHI for HMDB0040152 (3-Mercapto-1-hexanol)

Structure for HMDB0040152 (3-Mercapto-1-hexanol)

3D Structure for HMDB0040152 (3-Mercapto-1-hexanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra