MiMeDB: Showing metabocard for Methionine sulfone (MMDBc0000695)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:56 UTC

Update Date

2022-08-31 06:11:07 UTC

Metabolite ID

MMDBc0000695

Metabolite Identification

Common Name

Methionine sulfone

Description

Methionine sulfone, also known as S-dioxymethionine, 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 sulfone is a very strong basic compound (based on its pKa). Outside of the human body, Methionine sulfone has been detected, but not quantified in, garden onions. This could make methionine sulfone a potential biomarker for the consumption of these foods. An L-methionine derivative in which the sulfur has been oxidised to the corresponding sulfone.

Structure

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

Synonyms

Value	Source
(S)-Amino-4-(methylsulphonyl)butyric acid	ChEBI
L-2-Amino-4-(methylsulfonyl)butanoic acid	ChEBI
S-DIOXYMETHIONINE	ChEBI
(S)-Amino-4-(methylsulfonyl)butyrate	Generator
(S)-Amino-4-(methylsulfonyl)butyric acid	Generator
(S)-Amino-4-(methylsulphonyl)butyrate	Generator
L-2-Amino-4-(methylsulfonyl)butanoate	Generator
L-2-Amino-4-(methylsulphonyl)butanoate	Generator
L-2-Amino-4-(methylsulphonyl)butanoic acid	Generator
Methionine sulphone	Generator
L-Methionine sulfone	HMDB
(2S)-2-Amino-4-methanesulfonylbutanoate	HMDB
(2S)-2-Amino-4-methanesulphonylbutanoate	HMDB
(2S)-2-Amino-4-methanesulphonylbutanoic acid	HMDB
L-Methionine sulphone	HMDB
(±)-methionine sulfone	HMDB
2-Amino-4-(methylsulfonyl)butanoic acid	HMDB
DL-Methionine S,S-dioxide	HMDB
DL-Methionine sulfone	HMDB
(2S)-2-Amino-4-methanesulfonylbutanoic acid	HMDB
(2S)-2-Azaniumyl-4-methylsulfonylbutanoate	HMDB
(S)-Methionine sulfone	HMDB
L-Methionine-S-dioxide	HMDB

Molecular Formula

C₅H₁₁NO₄S

Average Mass

181.21

Monoisotopic Mass

181.040878535

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CS(=O)(=O)CC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO4S/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChI Key

UCUNFLYVYCGDHP-BYPYZUCNSA-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
Sulfone
Sulfonyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfone (CHEBI:21363 )
non-proteinogenic L-alpha-amino acid (CHEBI:21363 )
L-methionine derivative (CHEBI:21363 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	43.9 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-4.5	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	1.55	ChemAxon
pKa (Strongest Basic)	8.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.1 m³·mol⁻¹	ChemAxon
Polarizability	16.88 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	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0930000000-a8b2cb0213ee893d48ae	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0920000000-75355597daa1abd45a2b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-7930000000-bf8359c3bdba1ca22a19	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-9500000000-c9e8f48259346d75ae2a	2017-08-28	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 - LC-ESI-QTOF , negative	splash10-004i-9100000000-a64e4e4f00f558b8d041	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-053i-2900000000-86df25eea3b31b87c864	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0900000000-edb0612bd5e51f0ff33c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-4900000000-d01f2b5f78ac2aff34ef	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9800000000-847d87b54f39c753b902	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-7900000000-3f8cbe090d531b190c28	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-30baf7ca1241c843b112	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-3eaf623cbd0fb823070d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-5715fbecc01959b60d7d	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9500000000-26e0091d09aff775369c	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-b919c12731484cba0a9e	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-b31e53b325671bd96bf6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-0d5cfdf3520414f29369	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc7d5863f9883f681f45	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025270	Acetyl-CoA	Hydrogen Ion	L-methionine sulfoximine/L-methionine sulfone acetyltransferase	Acylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Bulb	Allium cepa	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.46	0.83	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	0.52	1.1	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0062174

DrugBank ID

DB03790

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019871

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-3739

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

445282

PDB ID

Not Available

ChEBI ID

21363

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Showing metabocard for Methionine sulfone (MMDBc0000695)

MOL for #<Metabolite:0x000055e06d345758>

3D MOL for #<Metabolite:0x000055e06d345758>

3D SDF for #<Metabolite:0x000055e06d345758>

3D-SDF for #<Metabolite:0x000055e06d345758>

PDB for #<Metabolite:0x000055e06d345758>

3D PDB for #<Metabolite:0x000055e06d345758>

SMILES for #<Metabolite:0x000055e06d345758>

INCHI for #<Metabolite:0x000055e06d345758>

Structure for #<Metabolite:0x000055e06d345758>

3D Structure for #<Metabolite:0x000055e06d345758>