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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:52:55 UTC

Update Date

2021-09-26 23:02:25 UTC

HMDB ID

HMDB0250776

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Methionine (S)-S-oxide

Description

Methionine sulfoxide belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia. Methionine sulfoxide is found, on average, in the highest concentration within a few different foods, such as barleys (Hordeum vulgare), green beans (Phaseolus vulgaris), and broccolis (Brassica oleracea var. italica) and in a lower concentration in red beetroots (Beta vulgaris var. rubra), red bell peppers (Capsicum annuum), and yellow bell peppers (Capsicum annuum). Methionine sulfoxide has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make methionine sulfoxide a potential biomarker for the consumption of these foods. Methionine sulfoxide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Methionine sulfoxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). D-methionine (s)-s-oxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically D-Methionine (S)-S-oxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methionine sulphoxide	Generator
Methionine sulfoxide, (+-)-isomer	MeSH
Methionine sulfoxide, (2R)-isomer	MeSH
Methionine sulfoxide, (2S)-isomer	MeSH
Methionine sulfoxide, (R-(r,s))-isomer	MeSH
Methionine sulfoxide, (S-(r,s))-isomer	MeSH
Methionine sulfoxide, 35S-labeled, (+-)-isomer	MeSH
2-amino-4-(Methylsulfinyl)-butanoate	HMDB
2-amino-4-(Methylsulfinyl)-butanoic acid	HMDB
alpha-amino-gamma-(Methylsulfinyl)-butyric acid	HMDB
DL-Methionine sulfoxide	HMDB
L-Methionine (S)-S-oxide	HMDB
L-Methionine R-oxide	HMDB
L-Methionine sulfoxide	HMDB
Met-so	HMDB
S-Oxide-methionine	HMDB

Chemical Formula

C₅H₁₁NO₃S

Average Molecular Weight

165.211

Monoisotopic Molecular Weight

165.045963913

IUPAC Name

2-amino-4-methanesulfinylbutanoic acid

Traditional Name

DL-methionine sulfoxide

CAS Registry Number

Not Available

SMILES

CS(=O)CCC(N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

InChI Key

QEFRNWWLZKMPFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methionine derivative (CHEBI:49033 )
S-oxide (CHEBI:49033 )
a small molecule (CPD0-1959 )

Ontology

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	-2.4	ALOGPS
logP	-4.6	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.34 m³·mol⁻¹	ChemAxon
Polarizability	16.04 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]+	129.279	30932474
DeepCCS	[M-H]-	125.829	30932474
DeepCCS	[M-2H]-	162.812	30932474
DeepCCS	[M+Na]+	137.9	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	132.6	32859911
AllCCS	[M+Na-2H]-	134.9	32859911
AllCCS	[M+HCOO]-	137.4	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Methionine (S)-S-oxide,1TMS,isomer #1	CS(=O)CCC(N)C(=O)O[Si](C)(C)C	1532.0	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,1TMS,isomer #1	CS(=O)CCC(N)C(=O)O[Si](C)(C)C	1675.4	Standard non polar	33892256
D-Methionine (S)-S-oxide,1TMS,isomer #1	CS(=O)CCC(N)C(=O)O[Si](C)(C)C	2491.4	Standard polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1636.6	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1843.5	Standard non polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1894.6	Standard polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1782.7	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1901.9	Standard non polar	33892256
D-Methionine (S)-S-oxide,2TMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2099.0	Standard polar	33892256
D-Methionine (S)-S-oxide,3TMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1797.6	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,3TMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2044.9	Standard non polar	33892256
D-Methionine (S)-S-oxide,3TMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1827.3	Standard polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2074.2	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2398.5	Standard non polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #1	CS(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2115.2	Standard polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2209.2	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2383.2	Standard non polar	33892256
D-Methionine (S)-S-oxide,2TBDMS,isomer #2	CS(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2227.5	Standard polar	33892256
D-Methionine (S)-S-oxide,3TBDMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2454.6	Semi standard non polar	33892256
D-Methionine (S)-S-oxide,3TBDMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2766.7	Standard non polar	33892256
D-Methionine (S)-S-oxide,3TBDMS,isomer #1	CS(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2182.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-6639ef576db5a01f8ee5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-4231d540eda02eebe871	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-f0849e8acf9a3e1e2763	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (3 TMS)	splash10-004i-1910000000-b7a64800b9e577e219d4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (Non-derivatized)	splash10-004i-1910000000-b7a64800b9e577e219d4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-a5138c4f03667c81645c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b8f17a35f754f6a2adff	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Methionine (S)-S-oxide GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-40d23196cb4ee1cad23f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-9300000000-40502e78936db0335f4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-05fs-9600000000-b39ca26ddac3482e7cc5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Methionine (S)-S-oxide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-9400000000-cac8577601b69f1b723a	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-9000000000-43361da834d0b07907fd	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00di-9000000000-6090b56aa5a22d72fb4f	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 10V, Negative-QTOF	splash10-03di-9300000000-fccbb5a2836a564cd61c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 20V, Negative-QTOF	splash10-03di-9000000000-74770a100fb96d6b7718	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 40V, Negative-QTOF	splash10-0002-9000000000-b39a3e60167512e82839	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 30V, Negative-QTOF	splash10-01ot-9000000000-7a9db4277879a8bd920b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 10V, Positive-QTOF	splash10-00xr-1900000000-f7bdaacb8f4c8c0ecac8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 20V, Positive-QTOF	splash10-0fk9-3900000000-0dbf2b087d6505b4b820	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 40V, Positive-QTOF	splash10-0a4i-9000000000-00dc8b47e3cb0dc2e321	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 10V, Negative-QTOF	splash10-03di-9600000000-9032163b7ca7799d7c43	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 20V, Negative-QTOF	splash10-03di-9000000000-562e35acb4f9e5564a69	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 40V, Negative-QTOF	splash10-03di-9000000000-2125dfc28681bc1d4c2e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 10V, Positive-QTOF	splash10-00di-9400000000-7375ade3d9a2e79890d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 20V, Positive-QTOF	splash10-0ab9-9000000000-4fa3654466563449190c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 40V, Positive-QTOF	splash10-0a4i-9000000000-375f7404d6c31bdf96b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 10V, Negative-QTOF	splash10-03di-9500000000-a4583e8c3a4365d330e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 20V, Negative-QTOF	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Methionine (S)-S-oxide 40V, Negative-QTOF	splash10-0006-9000000000-ff3de228e84a6b4470bc	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

FDB022789

KNApSAcK ID

C00051545

Chemspider ID

824

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1959

BiGG ID

Not Available

Wikipedia Link

Methionine sulfoxide

METLIN ID

Not Available

PubChem Compound

847

PDB ID

Not Available

ChEBI ID

49033

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for D-Methionine (S)-S-oxide (HMDB0250776)

MOL for HMDB0250776 (D-Methionine (S)-S-oxide)

3D MOL for HMDB0250776 (D-Methionine (S)-S-oxide)

3D SDF for HMDB0250776 (D-Methionine (S)-S-oxide)

3D-SDF for HMDB0250776 (D-Methionine (S)-S-oxide)

PDB for HMDB0250776 (D-Methionine (S)-S-oxide)

3D PDB for HMDB0250776 (D-Methionine (S)-S-oxide)

SMILES for HMDB0250776 (D-Methionine (S)-S-oxide)

INCHI for HMDB0250776 (D-Methionine (S)-S-oxide)

Structure for HMDB0250776 (D-Methionine (S)-S-oxide)

3D Structure for HMDB0250776 (D-Methionine (S)-S-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra