Milk Composition Database: Showing metabocard for Methionine sulfoxide (BMDB0002005)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:49:48 UTC

Update Date

2020-06-04 20:05:59 UTC

MCDB ID

BMDB0002005

Secondary Accession Numbers

BMDB02005

Metabolite Identification

Common Name

Methionine sulfoxide

Description

Methionine sulfoxide, also known as met-so or S-oxide-methionine, 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). Methionine sulfoxide exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Methionine sulfoxide exists in all living species, ranging from bacteria to humans.

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

165.21

Monoisotopic Molecular Weight

165.045964392

IUPAC Name

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

Traditional Name

L-methionine sulfoxide

CAS Registry Number

62697-73-8

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 )

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
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	1	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	Deposition Date	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	2019-05-22	View 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	2019-05-22	View 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	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1910000000-b7a64800b9e577e219d4	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-a5138c4f03667c81645c	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-b8f17a35f754f6a2adff	2019-05-22	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-40d23196cb4ee1cad23f	2019-05-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9400000000-cac8577601b69f1b723a	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-43361da834d0b07907fd	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-6090b56aa5a22d72fb4f	2019-05-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03kc-9400000000-f71dc9c687b7114eed8b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-9100000000-b03227c3dde8ee858ffb	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9500000000-a4583e8c3a4365d330e2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ff3de228e84a6b4470bc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000000-7375ade3d9a2e79890d4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-4fa3654466563449190c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-375f7404d6c31bdf96b3	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2019-05-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2019-05-22	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 26686724	details

External Links

HMDB ID

HMDB0002005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Showing metabocard for Methionine sulfoxide (BMDB0002005)

Structure for BMDB0002005 (Methionine sulfoxide)