Livestock Metabolome Database: Showing metabocard for Methionine sulfoxide (LMDB00373)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:23 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00373

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methionine sulfoxide

Description

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 is a very strong basic compound (based on its pKa). Methionine sulfoxide exists in all living species, ranging from bacteria to humans. Within humans, methionine sulfoxide participates in a number of enzymatic reactions. In particular, methionine sulfoxide can be biosynthesized from L-methionine through its interaction with the enzyme methionine-R-sulfoxide reductase B3. In addition, methionine sulfoxide can be biosynthesized from L-methionine; which is catalyzed by the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. Oxidation of methionine residues in tissue proteins can cause them to misfold or otherwise render them dysfunctional. In humans, methionine sulfoxide is involved in methionine metabolism. Thioredoxin serves to recycle by reduction some of the methionine sulfoxide reductase family of enzymes, whereas others can be reduced by metallothionein. Transgenically increasing the levels of MsrA in either the cytosol or the mitochondria had no significant effect on lifespan assessed by most standard statistical tests, and may possibly have led to early deaths in the cytosol-specific mice, although the survival curves appeared to suggest a slight increase in maximum (90%) survivorship, as did analysis using Boschloo's Exact test, a binomial test designed to test greater extreme variation. There is thus a rationale for thinking that by maintaining the structure, increased levels or activity of MsrA might retard the rate of aging. The oxidized residues tend to be arrayed around the active site and may guard access to this site by reactive oxygen species. The sulfur-containing amino acids methionine and cysteine are more easily oxidized than the other amino acids.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

165.211

Monoisotopic Molecular Weight

165.045963913

IUPAC Name

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

Traditional Name

L-methionine sulfoxide

CAS Registry Number

62697-73-8

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 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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted 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	15.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-6639ef576db5a01f8ee5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-4231d540eda02eebe871	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-f0849e8acf9a3e1e2763	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-1910000000-b7a64800b9e577e219d4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1910000000-b7a64800b9e577e219d4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-a5138c4f03667c81645c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b8f17a35f754f6a2adff	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-40d23196cb4ee1cad23f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9400000000-cac8577601b69f1b723a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-43361da834d0b07907fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-6090b56aa5a22d72fb4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03kc-9400000000-f71dc9c687b7114eed8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-9100000000-b03227c3dde8ee858ffb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9500000000-a4583e8c3a4365d330e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-433cb4a770ae8f69c615	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ff3de228e84a6b4470bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000000-7375ade3d9a2e79890d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-4fa3654466563449190c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-375f7404d6c31bdf96b3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	20.84 +/- 15.4 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	6.64 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	7.12 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	7.6 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	4.3644 +/- 3.3967 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.7581 +/- 2.6772 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.6844 +/- 2.2635 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.1889 +/- 2.0396 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.5452 +/- 2.2311 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.3533 +/- 2.9404 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.91 +/- 2.81 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	5.2467 +/- 2.8103 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.1712 +/- 2.3741 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.56 +/- 2.4806 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.7923 +/- 1.866 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.1381 +/- 1.9709 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0393 +/- 2.4802 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.41 uM	Not Available	Porcine	Barbara U. Metzle...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002005

FooDB ID

FDB022789

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD0-1959

METLIN ID

6428

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [12576054 ]

Showing metabocard for Methionine sulfoxide (LMDB00373)

Structure for LMDB00373 (Methionine sulfoxide)