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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:33 UTC

Update Date

2023-02-21 17:21:03 UTC

HMDB ID

HMDB0031634

Secondary Accession Numbers

HMDB31634

Metabolite Identification

Common Name

2-Propanethiol

Description

2-Propanethiol, also known as 2-mercaptopropane or 2-propylmercaptan, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. It can also be prepared by the reaction of sodium hydrosulfide with 1-chloropropane. 2-Propanethiol is a strong, gassy, and meaty tasting compound. 2-propanethiol has been detected, but not quantified, in potato. This could make 2-propanethiol a potential biomarker for the consumption of these foods. Propanethiol is an organic compound with the molecular formula C3H8S. Propanethiol is chemically classified among the thiols, which are organic compounds with molecular formulas and structural formulas similar to alcohols, except that sulfur-containing sulfhydryl group (-SH) replaces the oxygen-containing hydroxyl group in the molecule. It is highly flammable and it gives off irritating or toxic fumes (or gases) in a fire. It is a colorless liquid with a strong, offensive odor. Propanethiol's basic molecular formula is C3H7SH, and its structural formula is similar to that of the alcohol n-propanol. Propanethiol is manufactured commercially by the reaction of propene with hydrogen sulfide with ultraviolet light initiation in an anti-Markovnikov addition. It is moderately toxic and is less dense than water and slightly soluble in water. It is used as a feedstock for insecticides.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methylethanethiol	ChEBI
2-Mercaptopropane	ChEBI
2-Propylmercaptan	ChEBI
Isopropanethiol	ChEBI
Isopropyl mercaptan	ChEBI
Isopropylmercaptan	ChEBI
Isopropylthiol	ChEBI
2-Propylthiol	HMDB
iso-C3H7SH	HMDB
Propane-2-thiol	HMDB
Propanethiol-(2)	HMDB
2-Propanethiol	ChEBI

Chemical Formula

C₃H₈S

Average Molecular Weight

76.161

Monoisotopic Molecular Weight

76.034670946

IUPAC Name

propane-2-thiol

Traditional Name

2-propanethiol

CAS Registry Number

75-33-2

SMILES

CC(C)S

InChI Identifier

InChI=1S/C3H8S/c1-3(2)4/h3-4H,1-2H3

InChI Key

KJRCEJOSASVSRA-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

Hydrocarbon derivatives

Substituents

Alkylthiol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alkanethiol (CHEBI:8474 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031634)
Cytoplasm (HMDB: HMDB0031634)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031634)

Source

Endogenous

Endogenous (HMDB: HMDB0031634)

Plant

Plant (HMDB: HMDB0031634)

Exogenous

Food

Food (HMDB: HMDB0031634)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Exogenous (HMDB: HMDB0031634)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-130.7 °C	Not Available
Boiling Point	57.00 to 60.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4835 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.795 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.54 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.4	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	23.51 m³·mol⁻¹	ChemAxon
Polarizability	9.08 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]+	112.854	31661259
DarkChem	[M-H]-	106.795	31661259
DeepCCS	[M+H]+	127.337	30932474
DeepCCS	[M-H]-	125.326	30932474
DeepCCS	[M-2H]-	161.066	30932474
DeepCCS	[M+Na]+	135.723	30932474
AllCCS	[M+H]+	122.3	32859911
AllCCS	[M+H-H2O]+	117.9	32859911
AllCCS	[M+NH4]+	126.3	32859911
AllCCS	[M+Na]+	127.5	32859911
AllCCS	[M-H]-	152.8	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	167.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.7811 minutes	33406817
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	138.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1740.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	579.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	219.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	405.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	502.2 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	601.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	468.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1004.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.8 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	1187.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	660.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	532.9 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	147.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propanethiol	CC(C)S	740.6	Standard polar	33892256
2-Propanethiol	CC(C)S	535.2	Standard non polar	33892256
2-Propanethiol	CC(C)S	562.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Propanethiol,1TMS,isomer #1	CC(C)S[Si](C)(C)C	812.5	Semi standard non polar	33892256
2-Propanethiol,1TMS,isomer #1	CC(C)S[Si](C)(C)C	838.2	Standard non polar	33892256
2-Propanethiol,1TBDMS,isomer #1	CC(C)S[Si](C)(C)C(C)(C)C	1050.9	Semi standard non polar	33892256
2-Propanethiol,1TBDMS,isomer #1	CC(C)S[Si](C)(C)C(C)(C)C	1060.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propanethiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-4138219f3bc5bdc27d15	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propanethiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propanethiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9000000000-3b7220df0a10878b4b25	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 10V, Positive-QTOF	splash10-004i-9000000000-594b3178c8ca1bb1e1a3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 20V, Positive-QTOF	splash10-004i-9000000000-359ea8d4cf9aefc9f1eb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 40V, Positive-QTOF	splash10-0006-9000000000-341dbf2ebb39b22c8fc0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 10V, Negative-QTOF	splash10-004i-9000000000-a617e52a6e1a641de662	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 20V, Negative-QTOF	splash10-004i-9000000000-05c577ead761c7faf59c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 40V, Negative-QTOF	splash10-003r-9000000000-f9db64ff4a2b4ebc7536	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 10V, Negative-QTOF	splash10-004i-9000000000-e7c25eb55afb7cceba91	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 20V, Negative-QTOF	splash10-004i-9000000000-e7c25eb55afb7cceba91	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 40V, Negative-QTOF	splash10-004i-9000000000-9382ae4a769be47b0c3c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 10V, Positive-QTOF	splash10-004l-9000000000-82f4be8a3292f3cd09e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 20V, Positive-QTOF	splash10-004l-9000000000-bc42b0b2d7e6ade015ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propanethiol 40V, Positive-QTOF	splash10-0006-9000000000-25a31e4708559d04fe80	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Propanethiol

METLIN ID

Not Available

PubChem Compound

6364

PDB ID

Not Available

ChEBI ID

8474

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1049571

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 2-Propanethiol (HMDB0031634)

MOL for HMDB0031634 (2-Propanethiol)

3D MOL for HMDB0031634 (2-Propanethiol)

3D SDF for HMDB0031634 (2-Propanethiol)

3D-SDF for HMDB0031634 (2-Propanethiol)

PDB for HMDB0031634 (2-Propanethiol)

3D PDB for HMDB0031634 (2-Propanethiol)

SMILES for HMDB0031634 (2-Propanethiol)

INCHI for HMDB0031634 (2-Propanethiol)

Structure for HMDB0031634 (2-Propanethiol)

3D Structure for HMDB0031634 (2-Propanethiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra