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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:30:58 UTC

Update Date

2023-02-21 17:27:17 UTC

HMDB ID

HMDB0039965

Secondary Accession Numbers

HMDB39965

Metabolite Identification

Common Name

S-Propyl 2-propene-1-sulfinothioate

Description

S-Propyl 2-propene-1-sulfinothioate belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). S-Propyl 2-propene-1-sulfinothioate has been detected, but not quantified in, several different foods, such as garden onion (var.), garlics (Allium sativum), red onion, welsh onions (Allium fistulosum), and onion-family vegetables. This could make S-propyl 2-propene-1-sulfinothioate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on S-Propyl 2-propene-1-sulfinothioate.

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-Propyl 2-propene-1-sulfinothioic acid	Generator
S-Propyl 2-propene-1-sulphinothioate	Generator
S-Propyl 2-propene-1-sulphinothioic acid	Generator
1-[(Prop-2-ene-1-sulphinyl)sulphanyl]propane	HMDB

Chemical Formula

C₆H₁₂OS₂

Average Molecular Weight

164.289

Monoisotopic Molecular Weight

164.032956386

IUPAC Name

1-[(prop-2-ene-1-sulfinyl)sulfanyl]propane

Traditional Name

1-[(prop-2-ene-1-sulfinyl)sulfanyl]propane

CAS Registry Number

136516-43-3

SMILES

CCCSS(=O)CC=C

InChI Identifier

InChI=1S/C6H12OS2/c1-3-5-8-9(7)6-4-2/h4H,2-3,5-6H2,1H3

InChI Key

WIZBTKYLPUKXNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiosulfinic acid esters

Sub Class

Not Available

Direct Parent

Thiosulfinic acid esters

Alternative Parents

Substituents

Thiosulfinic acid ester
Allyl sulfur compound
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039965)
Cytoplasm (HMDB: HMDB0039965)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039965)

Source

Exogenous

Exogenous (HMDB: HMDB0039965)

Food

Food (HMDB: HMDB0039965)

Herb and spice

Herb

Garlic (FooDB: FOOD00008)
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: HMDB0039965)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039965)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1267 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.4 g/L	ALOGPS
logP	1.38	ALOGPS
logP	2.09	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-5.7	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	5	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	17.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	134.364	31661259
DarkChem	[M-H]-	131.003	31661259
DeepCCS	[M+H]+	139.684	30932474
DeepCCS	[M-H]-	137.691	30932474
DeepCCS	[M-2H]-	173.807	30932474
DeepCCS	[M+Na]+	148.565	30932474
AllCCS	[M+H]+	134.7	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	138.2	32859911
AllCCS	[M+Na]+	139.2	32859911
AllCCS	[M-H]-	140.4	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	146.5	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.	3.84 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9605 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1821.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	447.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	294.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	137.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.2 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	560.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1108.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	402.0 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	1174.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.3 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	27.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-Propyl 2-propene-1-sulfinothioate	CCCSS(=O)CC=C	1723.1	Standard polar	33892256
S-Propyl 2-propene-1-sulfinothioate	CCCSS(=O)CC=C	1225.5	Standard non polar	33892256
S-Propyl 2-propene-1-sulfinothioate	CCCSS(=O)CC=C	1189.8	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-Propyl 2-propene-1-sulfinothioate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-8b24227de71220988a06	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl 2-propene-1-sulfinothioate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 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-Propyl 2-propene-1-sulfinothioate 10V, Positive-QTOF	splash10-00or-9700000000-42ee1ad26472664930e5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 20V, Positive-QTOF	splash10-00dl-9500000000-cf8e5cd2f7adabcf975c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 40V, Positive-QTOF	splash10-002f-9000000000-395431c57945fb8b4676	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 10V, Negative-QTOF	splash10-0229-1900000000-3518b9d77a75fa1b72f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 20V, Negative-QTOF	splash10-00di-8900000000-086858fbfeff78e11431	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 40V, Negative-QTOF	splash10-000f-9100000000-5a5bcb925a9c118bff4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 10V, Negative-QTOF	splash10-004i-9000000000-ad38639e7a36b20c8e2a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 20V, Negative-QTOF	splash10-00b9-9000000000-44bd7cbe32adcc7b9de2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 40V, Negative-QTOF	splash10-01bi-9000000000-a75e80df42b4207b5c05	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 10V, Positive-QTOF	splash10-004i-9000000000-f8750c272f5965d3cc5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 20V, Positive-QTOF	splash10-002r-9000000000-5aec522b037d2fe63fcd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Propyl 2-propene-1-sulfinothioate 40V, Positive-QTOF	splash10-002f-9000000000-0b7b0a11e6e6a87960ea	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB019628

KNApSAcK ID

C00057037

Chemspider ID

35014904

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

58219334

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1881021

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-Propyl 2-propene-1-sulfinothioate (HMDB0039965)

MOL for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

3D MOL for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

3D SDF for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

3D-SDF for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

PDB for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

3D PDB for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

SMILES for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

INCHI for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

Structure for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

3D Structure for HMDB0039965 (S-Propyl 2-propene-1-sulfinothioate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra