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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:57:11 UTC

Update Date

2023-02-21 17:28:14 UTC

HMDB ID

HMDB0040413

Secondary Accession Numbers

HMDB40413

Metabolite Identification

Common Name

Ethyl 3-(methylthio)propanoate

Description

Ethyl 3-(methylthio)propanoate, also known as ethyl methyl mercaptopropionate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Ethyl 3-(methylthio)propanoate is a fruity, metallic, and pineapple tasting compound. Ethyl 3-(methylthio)propanoate is found, on average, in the highest concentration within pineapples (Ananas comosus). Ethyl 3-(methylthio)propanoate has also been detected, but not quantified in, several different foods, such as alcoholic beverages, asian pears (Pyrus pyrifolia), fruits, and milk and milk products. This could make ethyl 3-(methylthio)propanoate a potential biomarker for the consumption of these foods. Ethyl 3-(methylthio)propanoate 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 Ethyl 3-(methylthio)propanoate.

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-(Methylthio)propanoic acid ethyl ester	ChEBI
Ethyl 3-(methylmercapto)propionate	ChEBI
Ethyl methyl mercaptopropionate	ChEBI
3-(Methylthio)propanoate ethyl ester	Generator
Ethyl 3-(methylmercapto)propionic acid	Generator
Ethyl methyl mercaptopropionic acid	Generator
Ethyl 3-(methylthio)propanoic acid	Generator
Ethyl 3-(methylthio)propionate	ChEBI
Ethyl 3-methylmercaptopropionate	ChEBI
Ethyl 3-(methylthio)propionic acid	Generator
Ethyl 3-methylmercaptopropionic acid	Generator
3-(methylthio)Propionic acid ethylester	HMDB
Ethyl 3-(methylsulfanyl)propanoate	HMDB
Ethyl 3-methylthiopropanoate	HMDB
Ethyl beta -methylthiopropionate	HMDB
Ethyl beta-methylthiopropionate	HMDB
Ethyl methylthiopropanoate	HMDB
FEMA 3343	HMDB
Propanoic acid, 3-(methylthio)-, ethyl ester	HMDB
Propionic acid, 3-(methylthio)-, ethyl ester	HMDB
Ethyl 3-(methylthio)propanoate	ChEBI
Ethyl 3-methylthiopropionic acid	Generator

Chemical Formula

C₆H₁₂O₂S

Average Molecular Weight

148.223

Monoisotopic Molecular Weight

148.055800318

IUPAC Name

ethyl 3-(methylsulfanyl)propanoate

Traditional Name

ethyl 3-(methylsulfanyl)propanoate

CAS Registry Number

13327-56-5

SMILES

CCOC(=O)CCSC

InChI Identifier

InChI=1S/C6H12O2S/c1-3-8-6(7)4-5-9-2/h3-5H2,1-2H3

InChI Key

YSNWHRKJEKWJNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:87503 )
organosulfur compound (CHEBI:87503 )

Ontology

Not Available

Exogenous (HMDB: HMDB0040413)

Food

Fruit

Tropical fruit

Pineapple (FooDB: FOOD00012)

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	196.00 to 197.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4534 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.352 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.3 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.34	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.24 m³·mol⁻¹	ChemAxon
Polarizability	16.38 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]+	131.309	31661259
DarkChem	[M-H]-	127.824	31661259
DeepCCS	[M+H]+	135.642	30932474
DeepCCS	[M-H]-	133.46	30932474
DeepCCS	[M-2H]-	169.149	30932474
DeepCCS	[M+Na]+	143.704	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	129.1	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	136.5	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	142.5	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.	4.98 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8208 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1786.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	431.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	276.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	148.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	457.3 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	575.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1057.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	366.2 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	1132.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.6 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	58.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-(methylthio)propanoate	CCOC(=O)CCSC	1659.5	Standard polar	33892256
Ethyl 3-(methylthio)propanoate	CCOC(=O)CCSC	1122.9	Standard non polar	33892256
Ethyl 3-(methylthio)propanoate	CCOC(=O)CCSC	1132.2	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 - Ethyl 3-(methylthio)propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-9300000000-029e31417dd68f480b60	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-(methylthio)propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-(methylthio)propanoate 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 - Ethyl 3-(methylthio)propanoate 10V, Positive-QTOF	splash10-0f6t-1900000000-5bf8b1d6ee6320d4c1b4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 20V, Positive-QTOF	splash10-0zfs-9700000000-8bcaf49d26d088c50af9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 40V, Positive-QTOF	splash10-056s-9100000000-e0f8ca1ee495f433791b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 10V, Negative-QTOF	splash10-0002-9200000000-7645bab4e5fe8392cce3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 20V, Negative-QTOF	splash10-0002-9100000000-a4d3fefdf137fe9f1a0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 40V, Negative-QTOF	splash10-0002-9000000000-cce896b87192798ff9bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 10V, Negative-QTOF	splash10-0002-9300000000-5fb908dda705dda95183	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 40V, Negative-QTOF	splash10-0002-9000000000-fa0dccf82eb5be566ca7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 10V, Positive-QTOF	splash10-0w90-5900000000-49128a20cce7699fb3a6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 20V, Positive-QTOF	splash10-03di-9100000000-1ba654d4162c188e7c9e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-(methylthio)propanoate 40V, Positive-QTOF	splash10-01ot-9000000000-e1911524715c4e6b894a	2021-09-25	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB020145

KNApSAcK ID

Not Available

Chemspider ID

55501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61592

PDB ID

Not Available

ChEBI ID

87503

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008241

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 Ethyl 3-(methylthio)propanoate (HMDB0040413)

MOL for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

3D MOL for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

3D SDF for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

3D-SDF for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

PDB for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

3D PDB for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

SMILES for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

INCHI for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

Structure for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

3D Structure for HMDB0040413 (Ethyl 3-(methylthio)propanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra