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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

HMDB0032375

Secondary Accession Numbers

HMDB32375

Metabolite Identification

Common Name

(+/-)-4-Mercapto-4-methyl-2-pentanol

Description

(+/-)-4-Mercapto-4-methyl-2-pentanol, also known as 2-pentanol, 4-mercapto-4-methyl or 4-methyl-4-sulphanylpentan-2-ol, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Based on a literature review a significant number of articles have been published on (+/-)-4-Mercapto-4-methyl-2-pentanol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Pentanol, 4-mercapto-4-methyl	HMDB
4-Mercapto-4-methyl-2-pentanol	HMDB
4-Methyl-4-sulphanylpentan-2-ol	HMDB

Chemical Formula

C₆H₁₄OS

Average Molecular Weight

134.24

Monoisotopic Molecular Weight

134.07653576

IUPAC Name

4-methyl-4-sulfanylpentan-2-ol

Traditional Name

4-methyl-4-sulfanylpentan-2-ol

CAS Registry Number

31539-84-1

SMILES

CC(O)CC(C)(C)S

InChI Identifier

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

InChI Key

FDBQLLMYSACLPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Secondary alcohol
Alkylthiol
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032375)
Cytoplasm (HMDB: HMDB0032375)

Source

Endogenous

Endogenous (HMDB: HMDB0032375)

Exogenous

Food

Food (HMDB: HMDB0032375)

Exogenous (HMDB: HMDB0032375)

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	50.00 to 51.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	3939 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.278 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.89 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.01	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-2.5	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	39.02 m³·mol⁻¹	ChemAxon
Polarizability	15.46 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]+	128.456	31661259
DarkChem	[M-H]-	125.211	31661259
DeepCCS	[M+H]+	135.009	30932474
DeepCCS	[M-H]-	132.519	30932474
DeepCCS	[M-2H]-	168.518	30932474
DeepCCS	[M+Na]+	143.745	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	133.8	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	137.9	32859911
AllCCS	[M+HCOO]-	141.7	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.	2.76 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7508 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1792.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	408.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.8 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	448.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	844.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	334.4 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	1064.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	375.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	416.7 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	32.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-4-Mercapto-4-methyl-2-pentanol	CC(O)CC(C)(C)S	1591.8	Standard polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol	CC(O)CC(C)(C)S	959.2	Standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol	CC(O)CC(C)(C)S	994.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-4-Mercapto-4-methyl-2-pentanol,1TMS,isomer #1	CC(CC(C)(C)S)O[Si](C)(C)C	1112.2	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,1TMS,isomer #2	CC(O)CC(C)(C)S[Si](C)(C)C	1203.7	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,2TMS,isomer #1	CC(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1305.5	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,2TMS,isomer #1	CC(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C	1351.0	Standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,1TBDMS,isomer #1	CC(CC(C)(C)S)O[Si](C)(C)C(C)(C)C	1333.5	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,1TBDMS,isomer #2	CC(O)CC(C)(C)S[Si](C)(C)C(C)(C)C	1447.9	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,2TBDMS,isomer #1	CC(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1784.9	Semi standard non polar	33892256
(+/-)-4-Mercapto-4-methyl-2-pentanol,2TBDMS,isomer #1	CC(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1824.7	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-pentanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9100000000-39eed5425f0da0ba0d75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol GC-MS (1 TMS) - 70eV, Positive	splash10-01dl-9600000000-6e52a48817ae25fb080a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 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-pentanol 10V, Positive-QTOF	splash10-0159-3900000000-33f6971449b9bb943791	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 20V, Positive-QTOF	splash10-0159-7900000000-6b1513b64d0c1f1b099d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 40V, Positive-QTOF	splash10-001i-9200000000-12126cbee2fe967a2a54	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 10V, Negative-QTOF	splash10-001i-9800000000-e58a29e1ca78cdea79da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 20V, Negative-QTOF	splash10-001i-9600000000-bab987bc127ef8f3b464	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 40V, Negative-QTOF	splash10-001i-9100000000-8f2ed81cd6f42d8129d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 10V, Positive-QTOF	splash10-0f8i-9700000000-63012dc1b9ba3ed440ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 20V, Positive-QTOF	splash10-000x-9000000000-252a67c6efc74fbbb1f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 40V, Positive-QTOF	splash10-004l-9000000000-f027da0284ec376c7b88	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 10V, Negative-QTOF	splash10-0002-9000000000-8b828d93683e918aff46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 20V, Negative-QTOF	splash10-001i-9100000000-95115a839b97f5320e95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-4-Mercapto-4-methyl-2-pentanol 40V, Negative-QTOF	splash10-067i-9600000000-66e49b1cb7d7f3c786c3	2021-09-22	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

FDB009792

KNApSAcK ID

Not Available

Chemspider ID

4934681

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6429308

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1552021

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-4-methyl-2-pentanol (HMDB0032375)

MOL for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

3D MOL for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

3D SDF for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

3D-SDF for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

PDB for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

3D PDB for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

SMILES for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

INCHI for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

Structure for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

3D Structure for HMDB0032375 ((+/-)-4-Mercapto-4-methyl-2-pentanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra