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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:12:08 UTC

Update Date

2023-02-21 17:24:12 UTC

HMDB ID

HMDB0034377

Secondary Accession Numbers

HMDB34377

Metabolite Identification

Common Name

Methyl 3-(methylthio)propanoate

Description

Methyl 3-(methylthio)propanoate, also known as methyl beta -methylmercaptopropionate or fema 2720, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. Methyl 3-(methylthio)propanoate is found, on average, in the highest concentration within pineapples. This could make methyl 3-(methylthio)propanoate a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl 3-(methylthio)propanoic acid	Generator
3-Methylsulfanyl-propionic acid methyl ester	HMDB
3-Methylsulfanyl-propionate methyl ester	HMDB
3-Methylsulphanyl-propionate methyl ester	HMDB
3-Methylsulphanyl-propionic acid methyl ester	HMDB
3-(Methylthio)propanoic acid methyl ester	HMDB
FEMA 2720	HMDB
Methyl 3-(methylmercapto)propionate	HMDB
Methyl 3-(methylsulfanyl)propanoate	HMDB
Methyl 3-(methylthio)propionate	HMDB
Methyl 3-methylthiopropanoate	HMDB
Methyl 3-methylthiopropionate	HMDB
Methyl beta -methylmercaptopropionate	HMDB
Methyl beta -methylthiopropionate	HMDB
Methyl beta-methiopropionate	HMDB
Methyl beta-methylmercaptopropionate	HMDB
Methyl beta-methylthiopropionate	HMDB
Methyl ester OF 3-(methylthio)propanoic acid	HMDB
Methyl methylthiopropanoate	HMDB
Methyl-3-(methylthio)propionate	HMDB
Methyl-3-methylmercaptopropionate	HMDB
Propanoic acid, 3-(methylthio)-, methyl ester	HMDB
Propionic acid, 3-(methylthio)-, methyl ester	HMDB
Propionic acid, 3-(methylthio)-, methyl ester (8ci)	HMDB
Methyl 3-(methylsulfanyl)propanoic acid	HMDB
Methyl 3-(methylsulphanyl)propanoate	HMDB
Methyl 3-(methylsulphanyl)propanoic acid	HMDB
Methyl-b-methylthiopropionate	HMDB
Methyl-b-methylthiopropionic acid	HMDB
Methyl-beta-methylthiopropionic acid	HMDB
Methyl-β-methylthiopropionate	HMDB
Methyl-β-methylthiopropionic acid	HMDB

Chemical Formula

C₅H₁₀O₂S

Average Molecular Weight

134.197

Monoisotopic Molecular Weight

134.040150254

IUPAC Name

methyl 3-(methylsulfanyl)propanoate

Traditional Name

methyl 3-(methylsulfanyl)propanoate

CAS Registry Number

13532-18-8

SMILES

COC(=O)CCSC

InChI Identifier

InChI=1S/C5H10O2S/c1-7-5(6)3-4-8-2/h3-4H2,1-2H3

InChI Key

DMMJVMYCBULSIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Methyl esters

Alternative Parents

Substituents

Methyl 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

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0034377)

Food

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Endogenous (HMDB: HMDB0034377)

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	74.00 to 75.00 °C. @ 13.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	0.842 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	0.73	ALOGPS
logP	0.98	ChemAxon
logS	-1.1	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	4	ChemAxon
Refractivity	34.49 m³·mol⁻¹	ChemAxon
Polarizability	14.41 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]+	127.085	31661259
DarkChem	[M-H]-	123.126	31661259
DeepCCS	[M+H]+	131.675	30932474
DeepCCS	[M-H]-	129.54	30932474
DeepCCS	[M-2H]-	165.122	30932474
DeepCCS	[M+Na]+	139.687	30932474
AllCCS	[M+H]+	130.0	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	133.7	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	134.2	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	141.3	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.	4.5 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8599 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1695.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	396.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	269.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	380.0 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	537.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	976.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	341.9 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	1004.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	364.6 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	69.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-(methylthio)propanoate	COC(=O)CCSC	1552.8	Standard polar	33892256
Methyl 3-(methylthio)propanoate	COC(=O)CCSC	1057.3	Standard non polar	33892256
Methyl 3-(methylthio)propanoate	COC(=O)CCSC	1068.0	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 - Methyl 3-(methylthio)propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-13f2f62d0814467520cc	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 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 - Methyl 3-(methylthio)propanoate 10V, Positive-QTOF	splash10-0f79-2900000000-4e832d271171a7aad876	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 20V, Positive-QTOF	splash10-000i-9500000000-fc6001e286c89a081fa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 40V, Positive-QTOF	splash10-0a6r-9100000000-b3f08108acef20297649	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 10V, Negative-QTOF	splash10-0002-9200000000-16886e456d436d5d70e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 20V, Negative-QTOF	splash10-0002-9100000000-292f9d16150712448f12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 40V, Negative-QTOF	splash10-0002-9000000000-71e8eb706dd4eea9e25d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 10V, Positive-QTOF	splash10-0gw0-9700000000-719d5e9cacaade09311c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 20V, Positive-QTOF	splash10-08fr-9000000000-b5a6045ebd5cb11d791b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 40V, Positive-QTOF	splash10-0002-9000000000-0beb55df43a6882b5422	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 10V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-(methylthio)propanoate 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	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)	2021-09-25	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
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

FDB003806

KNApSAcK ID

Not Available

Chemspider ID

55549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61641

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1007021

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 Methyl 3-(methylthio)propanoate (HMDB0034377)

MOL for HMDB0034377 (Methyl 3-(methylthio)propanoate)

3D MOL for HMDB0034377 (Methyl 3-(methylthio)propanoate)

3D SDF for HMDB0034377 (Methyl 3-(methylthio)propanoate)

3D-SDF for HMDB0034377 (Methyl 3-(methylthio)propanoate)

PDB for HMDB0034377 (Methyl 3-(methylthio)propanoate)

3D PDB for HMDB0034377 (Methyl 3-(methylthio)propanoate)

SMILES for HMDB0034377 (Methyl 3-(methylthio)propanoate)

INCHI for HMDB0034377 (Methyl 3-(methylthio)propanoate)

Structure for HMDB0034377 (Methyl 3-(methylthio)propanoate)

3D Structure for HMDB0034377 (Methyl 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