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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2016-06-10 16:34:29 UTC

Update Date

2022-09-22 18:34:29 UTC

HMDB ID

HMDB0062174

Secondary Accession Numbers

HMDB62174

Metabolite Identification

Common Name

Methionine sulfone

Description

Methionine sulfone (CAS: 820-10-0), also known as L-methionine-S-dioxide, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha-amino acids which have the L-configuration at the alpha-carbon atom. Methionine sulfone is a very strong basic compound (based on its pKa). Methionine sulfone has been detected, but not quantified, in garden onions. This could make methionine sulfone 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
(S)-Amino-4-(methylsulphonyl)butyric acid	ChEBI
L-2-Amino-4-(methylsulfonyl)butanoic acid	ChEBI
S-DIOXYMETHIONINE	ChEBI
(S)-Amino-4-(methylsulfonyl)butyrate	Generator
(S)-Amino-4-(methylsulfonyl)butyric acid	Generator
(S)-Amino-4-(methylsulphonyl)butyrate	Generator
L-2-Amino-4-(methylsulfonyl)butanoate	Generator
L-2-Amino-4-(methylsulphonyl)butanoate	Generator
L-2-Amino-4-(methylsulphonyl)butanoic acid	Generator
Methionine sulphone	Generator
L-Methionine sulfone	HMDB
(2S)-2-Amino-4-methanesulfonylbutanoate	HMDB
(2S)-2-Amino-4-methanesulphonylbutanoate	HMDB
(2S)-2-Amino-4-methanesulphonylbutanoic acid	HMDB
L-Methionine sulphone	HMDB
(±)-methionine sulfone	HMDB
2-Amino-4-(methylsulfonyl)butanoic acid	HMDB
DL-Methionine S,S-dioxide	HMDB
DL-Methionine sulfone	HMDB
(2S)-2-Amino-4-methanesulfonylbutanoic acid	HMDB
(2S)-2-Azaniumyl-4-methylsulfonylbutanoate	HMDB
(S)-Methionine sulfone	HMDB
L-Methionine-S-dioxide	HMDB

Chemical Formula

C₅H₁₁NO₄S

Average Molecular Weight

181.21

Monoisotopic Molecular Weight

181.040878535

IUPAC Name

(2S)-2-amino-4-methanesulfonylbutanoic acid

Traditional Name

(2S)-2-amino-4-methanesulfonylbutanoic acid

CAS Registry Number

7314-32-1

SMILES

CS(=O)(=O)CC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO4S/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChI Key

UCUNFLYVYCGDHP-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Sulfone
Sulfonyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfone (CHEBI:21363 )
non-proteinogenic L-alpha-amino acid (CHEBI:21363 )
L-methionine derivative (CHEBI:21363 )

Ontology

Not Available

Urine (PMID: 27012787)
Feces (PMID: 27543620)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

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	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-3.2	ALOGPS
logP	-4.5	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	1.55	ChemAxon
pKa (Strongest Basic)	8.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.1 m³·mol⁻¹	ChemAxon
Polarizability	16.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.903	30932474
DeepCCS	[M-H]-	129.642	30932474
DeepCCS	[M-2H]-	166.561	30932474
DeepCCS	[M+Na]+	142.099	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.9	32859911
AllCCS	[M+NH4]+	143.1	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	137.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methionine sulfone	CS(=O)(=O)CC[C@H](N)C(O)=O	2492.8	Standard polar	33892256
Methionine sulfone	CS(=O)(=O)CC[C@H](N)C(O)=O	1473.1	Standard non polar	33892256
Methionine sulfone	CS(=O)(=O)CC[C@H](N)C(O)=O	1892.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methionine sulfone,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCS(C)(=O)=O	1650.9	Semi standard non polar	33892256
Methionine sulfone,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O	1695.5	Semi standard non polar	33892256
Methionine sulfone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C	1741.7	Semi standard non polar	33892256
Methionine sulfone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C	1864.5	Standard non polar	33892256
Methionine sulfone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C	2361.7	Standard polar	33892256
Methionine sulfone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C	1863.7	Semi standard non polar	33892256
Methionine sulfone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C	1916.3	Standard non polar	33892256
Methionine sulfone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C	2551.5	Standard polar	33892256
Methionine sulfone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C)[Si](C)(C)C	1910.1	Semi standard non polar	33892256
Methionine sulfone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C)[Si](C)(C)C	2083.8	Standard non polar	33892256
Methionine sulfone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C)[Si](C)(C)C	2172.8	Standard polar	33892256
Methionine sulfone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCS(C)(=O)=O	1904.7	Semi standard non polar	33892256
Methionine sulfone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O	1947.7	Semi standard non polar	33892256
Methionine sulfone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C(C)(C)C	2206.8	Semi standard non polar	33892256
Methionine sulfone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C(C)(C)C	2399.3	Standard non polar	33892256
Methionine sulfone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(C)(=O)=O)C(=O)O[Si](C)(C)C(C)(C)C	2481.6	Standard polar	33892256
Methionine sulfone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2326.4	Semi standard non polar	33892256
Methionine sulfone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2436.8	Standard non polar	33892256
Methionine sulfone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CCS(C)(=O)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2567.7	Standard polar	33892256
Methionine sulfone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2588.5	Semi standard non polar	33892256
Methionine sulfone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2861.9	Standard non polar	33892256
Methionine sulfone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(C)(=O)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2435.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methionine sulfone EI-B (Non-derivatized)	splash10-004i-0930000000-a8b2cb0213ee893d48ae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfone GC-EI-TOF (Non-derivatized)	splash10-004i-0920000000-75355597daa1abd45a2b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfone GC-EI-TOF (Non-derivatized)	splash10-00b9-7930000000-bf8359c3bdba1ca22a19	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methionine sulfone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-9500000000-c9e8f48259346d75ae2a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methionine sulfone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfone LC-ESI-QTOF , negative-QTOF	splash10-004i-9100000000-a64e4e4f00f558b8d041	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfone LC-ESI-QTOF , positive-QTOF	splash10-053i-2900000000-86df25eea3b31b87c864	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 10V, Positive-QTOF	splash10-0019-0900000000-edb0612bd5e51f0ff33c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 20V, Positive-QTOF	splash10-05n0-4900000000-d01f2b5f78ac2aff34ef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 40V, Positive-QTOF	splash10-0a4i-9800000000-847d87b54f39c753b902	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 10V, Negative-QTOF	splash10-003r-7900000000-3f8cbe090d531b190c28	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 20V, Negative-QTOF	splash10-004i-9100000000-30baf7ca1241c843b112	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 40V, Negative-QTOF	splash10-004i-9000000000-3eaf623cbd0fb823070d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 10V, Positive-QTOF	splash10-000i-1900000000-5715fbecc01959b60d7d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 20V, Positive-QTOF	splash10-0a4r-9500000000-26e0091d09aff775369c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 40V, Positive-QTOF	splash10-0a4i-9000000000-b919c12731484cba0a9e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 10V, Negative-QTOF	splash10-001i-2900000000-b31e53b325671bd96bf6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 20V, Negative-QTOF	splash10-004i-9200000000-0d5cfdf3520414f29369	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfone 40V, Negative-QTOF	splash10-004i-9000000000-fc7d5863f9883f681f45	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)	2021-09-24	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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.52-1.1 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.46-0.83 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03790

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019871

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-3739

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

445282

PDB ID

Not Available

ChEBI ID

21363

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Methionine sulfone (HMDB0062174)

MOL for HMDB0062174 (Methionine sulfone)

3D MOL for HMDB0062174 (Methionine sulfone)

3D SDF for HMDB0062174 (Methionine sulfone)

3D-SDF for HMDB0062174 (Methionine sulfone)

PDB for HMDB0062174 (Methionine sulfone)

3D PDB for HMDB0062174 (Methionine sulfone)

SMILES for HMDB0062174 (Methionine sulfone)

INCHI for HMDB0062174 (Methionine sulfone)

Structure for HMDB0062174 (Methionine sulfone)

3D Structure for HMDB0062174 (Methionine sulfone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra