Human Metabolome Database: Showing metabocard for Methionine sulfoxide (HMDB0002005)

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

enzymes (3) Show 3 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2020-02-27 16:50:44 UTC

HMDB ID

HMDB0002005

Secondary Accession Numbers

HMDB02005

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 through the action of the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia.

Structure

MOL SDF PDB SMILES InChI

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

Disposition

Route of exposure:

Enteral:

Ingestion

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Methionine Metabolism

Physical Properties

State

Solid

Experimental 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

Predicted 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

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
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
1D NMR	1H 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

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Epidermis
Placenta

Pathways

Name	SMPDB/Pathwhiz	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	Molecular You	details
Blood	Detected and Quantified	4.0 (3.0-5.0) uM	Adult (>18 years old)	Not Specified	Normal	12576054	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but 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	Mordechai, Hien, ...	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	López Hernández Y...	details
Urine	Detected and Quantified	1.48 +/- 0.80 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	López Hernández Y...	details
Urine	Detected and Quantified	1.67 +/- 0.69 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	López Hernández Y...	details
Urine	Detected and Quantified	< 0.132 umol/mmol creatinine	Adult (>18 years old)	Both	Normal		details
Urine	Detected and Quantified	0.31 (0.14-0.66) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but 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	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.4259 +/- 0.5426 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

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
(). Mordechai, Hien, and David S. Wishart. .

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

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 ]

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)

Structure for HMDB0002005 (Methionine sulfoxide)

Enzymes

Reactions