Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2023-05-30 20:55:52 UTC

HMDB ID

HMDB0002005

Secondary Accession Numbers

HMDB02005

Metabolite Identification

Common Name

Methionine sulfoxide

Description

Methionine sulfoxide (MetO) or L-Methionine sulfoxide 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. Methionine sulfoxide arises through the oxidation of methionine residues in proteins by reactive oxygen species (ROS). Oxidation of methionine results in a mixture of the two diastereomers methionine-S-sulfoxide and methionine-R-sulfoxide. Methionine oxidation is considered an important post-translational event in protein synthesis and can affect the function and activity of many proteins. The oxidation of methionine plays an important role in vivo, during biological conditions of oxidative stress, as well as for protein stability in vitro. For instance, the oxidation of methionine residues in tissue proteins can cause them to misfold or otherwise render them dysfunctional. Most organisms have developed systems to restore these oxidized methionine residues back to methionine (i.e., converting MetO to Met). This reduction is done by the methionine sulfoxide reductase (MSR) system, with the MSRs type A (MSRA) and type B (MSRB) being specific for the S and R forms of MetO, respectively (PMID: 28917052 ). In mammals, the selenoprotein MSRB1 plays an important MetO repair function, and its expression is tightly regulated by dietary selenium (PMID: 28917052 ). The eventual proteolyis of any unfolded or misfolded MetO modified proteins leads to the production of free methionine sulfoxide that can be detected in blood or urine. MetO is not a proteogenic amino acid and cannot be incorporated into proteins during ribosomal mediated translation. Levels of free MetO are closely correlated with levels of oxidative stress. Methionine sulfoxide (MetO), increases with age in body tissues, and its presence is believed by some to contribute to biological aging. Levels of MetO are also increased in individuals suffering from chronic bacterial infections (tuberculosis) or other conditions causing inflammation (PMID: 32123207 ). Similarly, MetO is increased in the serum/plasma of patients diagnosed with sepsis (PMID: 27501420 ). This likely reflects the high production of ROS species arising from the overactive (but underperforming) immune response.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Methionine sulfoxide	ChEBI
Methionine S-oxide	ChEBI
L-Methionine sulphoxide	Generator
Methionine sulphoxide	Generator
Methionine sulfoxide, (R-(r,s))-isomer	HMDB
Methionine sulfoxide, 35S-labeled, (+-)-isomer	HMDB
Methionine sulfoxide, (S-(r,s))-isomer	HMDB
Methionine sulfoxide, (2S)-isomer	HMDB
Methionine sulfoxide, (2R)-isomer	HMDB
Methionine sulfoxide, (+-)-isomer	HMDB
DL-Methionine sulfoxide	HMDB
L-Methionine S-oxide	HMDB
Methionine sulfoxide	HMDB

Chemical Formula

C₅H₁₁NO₃S

Average Molecular Weight

165.21

Monoisotopic Molecular Weight

165.045964392

IUPAC Name

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

Traditional Name

L-methionine sulfoxide

CAS Registry Number

3226-65-1

SMILES

CS(=O)CC[C@H](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)/t4-,10?/m0/s1

InChI Key

QEFRNWWLZKMPFJ-YGVKFDHGSA-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
Sulfoxide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methionine S-oxide (CHEBI:17016 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12576054)
Saliva (HMDB: HMDB0002005)

Tissue

Epithelium

Epidermis (HMDB: HMDB0002005)

Organ

Placenta (HMDB: HMDB0002005)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0002005)

Source

Endogenous

Endogenous (HMDB: HMDB0002005)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Fruit vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)
Carrot (FooDB: FOOD00245)

Cabbage

Broccoli (FooDB: FOOD00034)
White cabbage (FooDB: FOOD00887)

Leaf vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Gourd

Cucumber (FooDB: FOOD00065)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Turnip (FooDB: FOOD00036)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Fruit

Berry

Saskatoon berry (FooDB: FOOD00884)

Process

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	232 - 234 °C	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
Water Solubility	54 g/L	ALOGPS
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	15.98 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]+	130.024	30932474
DeepCCS	[M-H]-	126.197	30932474
DeepCCS	[M-2H]-	163.584	30932474
DeepCCS	[M+Na]+	139.063	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

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methionine sulfoxide	CS(=O)CC[C@H](N)C(O)=O	2488.8	Standard polar	33892256
Methionine sulfoxide	CS(=O)CC[C@H](N)C(O)=O	1392.4	Standard non polar	33892256
Methionine sulfoxide	CS(=O)CC[C@H](N)C(O)=O	1650.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methionine sulfoxide,1TMS,isomer #1	CS(=O)CC[C@H](N)C(=O)O[Si](C)(C)C	1518.3	Semi standard non polar	33892256
Methionine sulfoxide,1TMS,isomer #2	CS(=O)CC[C@H](N[Si](C)(C)C)C(=O)O	1580.5	Semi standard non polar	33892256
Methionine sulfoxide,2TMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1645.4	Semi standard non polar	33892256
Methionine sulfoxide,2TMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1903.5	Standard non polar	33892256
Methionine sulfoxide,2TMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1942.3	Standard polar	33892256
Methionine sulfoxide,2TMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1750.5	Semi standard non polar	33892256
Methionine sulfoxide,2TMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1925.5	Standard non polar	33892256
Methionine sulfoxide,2TMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2115.4	Standard polar	33892256
Methionine sulfoxide,3TMS,isomer #1	CS(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1788.4	Semi standard non polar	33892256
Methionine sulfoxide,3TMS,isomer #1	CS(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2078.6	Standard non polar	33892256
Methionine sulfoxide,3TMS,isomer #1	CS(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1834.3	Standard polar	33892256
Methionine sulfoxide,1TBDMS,isomer #1	CS(=O)CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1758.8	Semi standard non polar	33892256
Methionine sulfoxide,1TBDMS,isomer #2	CS(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1815.9	Semi standard non polar	33892256
Methionine sulfoxide,2TBDMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2082.8	Semi standard non polar	33892256
Methionine sulfoxide,2TBDMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2460.1	Standard non polar	33892256
Methionine sulfoxide,2TBDMS,isomer #1	CS(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2135.6	Standard polar	33892256
Methionine sulfoxide,2TBDMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2192.9	Semi standard non polar	33892256
Methionine sulfoxide,2TBDMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2431.8	Standard non polar	33892256
Methionine sulfoxide,2TBDMS,isomer #2	CS(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2223.9	Standard polar	33892256
Methionine sulfoxide,3TBDMS,isomer #1	CS(=O)CC[C@@H](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	2463.4	Semi standard non polar	33892256
Methionine sulfoxide,3TBDMS,isomer #1	CS(=O)CC[C@@H](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	2800.8	Standard non polar	33892256
Methionine sulfoxide,3TBDMS,isomer #1	CS(=O)CC[C@@H](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	2190.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-6639ef576db5a01f8ee5	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-4231d540eda02eebe871	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-f0849e8acf9a3e1e2763	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-MS (3 TMS)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-MS (Non-derivatized)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-a5138c4f03667c81645c	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b8f17a35f754f6a2adff	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methionine sulfoxide GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-40d23196cb4ee1cad23f	2019-05-22	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methionine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methionine sulfoxide 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 sulfoxide Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-9400000000-cac8577601b69f1b723a	2019-05-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfoxide Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-9000000000-43361da834d0b07907fd	2019-05-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfoxide Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00di-9000000000-6090b56aa5a22d72fb4f	2019-05-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfoxide 35V, Negative-QTOF	splash10-03kc-9400000000-f71dc9c687b7114eed8b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methionine sulfoxide 35V, Positive-QTOF	splash10-0a4i-9100000000-b03227c3dde8ee858ffb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 10V, Negative-QTOF	splash10-03di-9500000000-a4583e8c3a4365d330e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 20V, Negative-QTOF	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 40V, Negative-QTOF	splash10-0006-9000000000-ff3de228e84a6b4470bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 10V, Positive-QTOF	splash10-00di-9400000000-7375ade3d9a2e79890d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 20V, Positive-QTOF	splash10-0ab9-9000000000-4fa3654466563449190c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methionine sulfoxide 40V, Positive-QTOF	splash10-0a4i-9000000000-375f7404d6c31bdf96b3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2019-05-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2019-05-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Epidermis
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency		Not Available
Hypermethioninemia		Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency		Not Available
Glycine N-methyltransferase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.30-1.40 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	4.0 (3.0-5.0) uM	Adult (>18 years old)	Not Specified	Normal	12576054	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	110 +/- 80 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	20 +/- 10 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.0444 +/- 0.0842 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.110 +/- 0.126 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	3.28 +/- 1.20 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.6418 +/- 0.4235 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.00-7.88 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	0.6-3.59 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	1.48 +/- 0.80 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	1.67 +/- 0.69 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	< 0.132 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	0.52 (0.21-0.99) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.31 (0.14-0.66) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2(1.4-18) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.5038 +/- 0.5427 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.4259 +/- 0.5426 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022789

KNApSAcK ID

Not Available

Chemspider ID

139840

KEGG Compound ID

C02989

BioCyc ID

CPD0-1959

BiGG ID

Not Available

Wikipedia Link

Methionine sulfoxide

METLIN ID

6428

PubChem Compound

158980

PDB ID

Not Available

ChEBI ID

17016

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)

Download (PDF)

General References

Schallreuter KU: Functioning methionine-S-sulfoxide reductases A and B are present in human skin. J Invest Dermatol. 2006 May;126(5):947-9. [PubMed:16619011 ]
O'Donohue TL, Charlton CG, Thoa NB, Helke CJ, Moody TW, Pert A, Williams A, Miller RL, Jacobowitz DM: Release of alpha-melanocyte stimulating hormone into rat and human cerebrospinal fluid in vivo and from rat hypothalamus slices in vitro. Peptides. 1981 Spring;2(1):93-100. [PubMed:7243627 ]
Boudier C, Cadene M, Bieth JG: Inhibition of neutrophil cathepsin G by oxidized mucus proteinase inhibitor. Effect of heparin. Biochemistry. 1999 Jun 29;38(26):8451-7. [PubMed:10387091 ]
Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. [PubMed:12576054 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
Tarrago L, Oheix E, Peterfi Z, Gladyshev VN: Monitoring of Methionine Sulfoxide Content and Methionine Sulfoxide Reductase Activity. Methods Mol Biol. 2018;1661:285-299. doi: 10.1007/978-1-4939-7258-6_20. [PubMed:28917052 ]
Cho Y, Park Y, Sim B, Kim J, Lee H, Cho SN, Kang YA, Lee SG: Identification of serum biomarkers for active pulmonary tuberculosis using a targeted metabolomics approach. Sci Rep. 2020 Mar 2;10(1):3825. doi: 10.1038/s41598-020-60669-0. [PubMed:32123207 ]

Enzymes

Enzyme Details

1. Mitochondrial peptide methionine sulfoxide reductase

General function:: Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
Specific function:: Has an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine.
Gene Name:: MSRA
Uniprot ID:: Q9UJ68
Molecular weight:: 21737.41

Reactions

L-Methionine + thioredoxin disulfide + Water → Methionine sulfoxide + thioredoxin	details

Enzyme Details

2. Methionine-R-sulfoxide reductase B2, mitochondrial

General function:: Involved in peptide-methionine-(S)-S-oxide reductase activity
Specific function:: Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine (By similarity). Upon oxidative stress, may play a role in the preservation of mitochondrial integrity by decreasing the intracellular reactive oxygen species build-up through its scavenging role, hence contributing to cell survival and protein maintenance.
Gene Name:: MSRB2
Uniprot ID:: Q9Y3D2
Molecular weight:: 19536.055

Enzyme Details

3. Methionine-R-sulfoxide reductase B3

General function:: Involved in peptide-methionine-(S)-S-oxide reductase activity
Specific function:: Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine. Isoform 2 is essential for hearing.
Gene Name:: MSRB3
Uniprot ID:: Q8IXL7
Molecular weight:: 20010.23

Showing metabocard for Methionine sulfoxide (HMDB0002005)

MOL for HMDB0002005 (Methionine sulfoxide)

3D MOL for HMDB0002005 (Methionine sulfoxide)

3D SDF for HMDB0002005 (Methionine sulfoxide)

3D-SDF for HMDB0002005 (Methionine sulfoxide)

PDB for HMDB0002005 (Methionine sulfoxide)

3D PDB for HMDB0002005 (Methionine sulfoxide)

SMILES for HMDB0002005 (Methionine sulfoxide)

INCHI for HMDB0002005 (Methionine sulfoxide)

Structure for HMDB0002005 (Methionine sulfoxide)

3D Structure for HMDB0002005 (Methionine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions