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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:44:41 UTC

Update Date

2023-02-21 17:25:50 UTC

HMDB ID

HMDB0037493

Secondary Accession Numbers

HMDB37493

Metabolite Identification

Common Name

S-2-Propenyl propanethioate

Description

S-2-Propenyl propanethioate belongs to the class of organic compounds known as thioesters. These are organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR' (R=H, alkyl, aryl; R'=alkyl, aryl; X=O,S). S-2-Propenyl propanethioate is a sweet, fresh, and garlic tasting compound. Based on a literature review very few articles have been published on S-2-Propenyl propanethioate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
S-2-Propenyl propanethioic acid	Generator
Allyl thiopropionate	HMDB
FEMA 3329	HMDB
Propanethioic acid, S-2-propenyl ester	HMDB
S-Allyl propanethioate	HMDB
S-Allyl thiopropionate	HMDB
Thioacrylic propionate	HMDB
1-(Prop-2-en-1-ylsulphanyl)propan-1-one	Generator

Chemical Formula

C₆H₁₀OS

Average Molecular Weight

130.208

Monoisotopic Molecular Weight

130.045235632

IUPAC Name

1-(prop-2-en-1-ylsulfanyl)propan-1-one

Traditional Name

1-(prop-2-en-1-ylsulfanyl)propan-1-one

CAS Registry Number

41820-22-8

SMILES

CCC(=O)SCC=C

InChI Identifier

InChI=1S/C6H10OS/c1-3-5-8-6(7)4-2/h3H,1,4-5H2,2H3

InChI Key

GKRISGLFPMFKSX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioesters. These are organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR' (R=H, alkyl, aryl; R'=alkyl, aryl; X=O,S).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiocarboxylic acids and derivatives

Sub Class

Thioesters

Direct Parent

Thioesters

Alternative Parents

Substituents

Allyl sulfur compound
Carbothioic s-ester
Thiocarboxylic acid ester
Sulfenyl compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037493)
Cytoplasm (HMDB: HMDB0037493)

Source

Exogenous

Exogenous (HMDB: HMDB0037493)

Food

Food (HMDB: HMDB0037493)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037493)

Biological role

Nutrient (HMDB: HMDB0037493)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	150.00 to 151.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4266 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.089 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	1.72	ALOGPS
logP	2.01	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.55 m³·mol⁻¹	ChemAxon
Polarizability	14.42 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]+	128.446	31661259
DarkChem	[M-H]-	122.883	31661259
DeepCCS	[M+H]+	128.42	30932474
DeepCCS	[M-H]-	126.346	30932474
DeepCCS	[M-2H]-	162.016	30932474
DeepCCS	[M+Na]+	136.736	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	125.2	32859911
AllCCS	[M+NH4]+	133.0	32859911
AllCCS	[M+Na]+	134.1	32859911
AllCCS	[M-H]-	132.1	32859911
AllCCS	[M+Na-2H]-	135.4	32859911
AllCCS	[M+HCOO]-	139.1	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.	4.57 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6251 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	42.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1745.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	485.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	335.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.7 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	604.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1102.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	394.3 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	1168.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	478.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	486.6 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	57.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-2-Propenyl propanethioate	CCC(=O)SCC=C	1407.3	Standard polar	33892256
S-2-Propenyl propanethioate	CCC(=O)SCC=C	960.7	Standard non polar	33892256
S-2-Propenyl propanethioate	CCC(=O)SCC=C	986.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-2-Propenyl propanethioate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-1087e4c8476963e6fa9a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-2-Propenyl propanethioate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-2-Propenyl propanethioate 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 - S-2-Propenyl propanethioate 10V, Positive-QTOF	splash10-009x-9400000000-6c875c5c4c3427660cdb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 20V, Positive-QTOF	splash10-052f-9100000000-b5bb14cd3b6c039c4e04	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 40V, Positive-QTOF	splash10-006x-9000000000-9e6f46f4f60e49e61a6d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 10V, Negative-QTOF	splash10-00b9-9500000000-5c9732702b6bac29b968	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 20V, Negative-QTOF	splash10-0ab9-9200000000-10dc808c6a93063d2902	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 40V, Negative-QTOF	splash10-0a4r-9000000000-676fbdb0088559178c0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 10V, Positive-QTOF	splash10-0kmi-9200000000-c1fb21b0d868d76ad7a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 20V, Positive-QTOF	splash10-00dl-9000000000-75679a2a6dfda49ea7ad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 40V, Positive-QTOF	splash10-000f-9000000000-e35be446a0247af9b903	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 10V, Negative-QTOF	splash10-00di-9000000000-f8d47443ee219049a75b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 20V, Negative-QTOF	splash10-053r-9000000000-f06db63fc864ca071e26	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-2-Propenyl propanethioate 40V, Negative-QTOF	splash10-000i-9000000000-a06b3094bbb13ccb2c81	2021-09-25	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+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

FDB016568

KNApSAcK ID

Not Available

Chemspider ID

55843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61995

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003001

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 S-2-Propenyl propanethioate (HMDB0037493)

MOL for HMDB0037493 (S-2-Propenyl propanethioate)

3D MOL for HMDB0037493 (S-2-Propenyl propanethioate)

3D SDF for HMDB0037493 (S-2-Propenyl propanethioate)

3D-SDF for HMDB0037493 (S-2-Propenyl propanethioate)

PDB for HMDB0037493 (S-2-Propenyl propanethioate)

3D PDB for HMDB0037493 (S-2-Propenyl propanethioate)

SMILES for HMDB0037493 (S-2-Propenyl propanethioate)

INCHI for HMDB0037493 (S-2-Propenyl propanethioate)

Structure for HMDB0037493 (S-2-Propenyl propanethioate)

3D Structure for HMDB0037493 (S-2-Propenyl propanethioate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra