Human Metabolome Database: Showing metabocard for Dimethyl sulfone (HMDB0004983)

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

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-09-13 08:28:37 UTC

Update Date

2020-05-28 23:12:08 UTC

HMDB ID

HMDB0004983

Secondary Accession Numbers

HMDB0006702
HMDB04983
HMDB06702

Metabolite Identification

Common Name

Dimethyl sulfone

Description

Dimethyl sulfone (DMSO2) or methylsulfonylmethane (MSM), is an organic sulfur compound belonging to a class of chemicals known as sulfones. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a metabolite occurring in plasma and CSF of normal human. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. (PMID 15996001 ). Dimethyl sulfone can be found in Afipia (Wikipedia ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dimethyl sulphone	ChEBI
Methylsulfonylmethane	ChEBI
Sulfonylbismethane	ChEBI
Sulphonylbismethane	ChEBI
Methylsulphonylmethane	Generator
(Methylsulfonyl)methane	HMDB
Dimethylsulfone	HMDB
Lignisul MSM	HMDB
Methyl sulfone	HMDB
Opti MSM	HMDB
Sulfonylbis-methane	HMDB
Methyl sulfonmethane	HMDB
Dimethyl sulfone, 13C-labeled	HMDB
Sulphonyldimethane	HMDB
Dimethyl sulfone	ChEBI

Chemical Formula

C₂H₆O₂S

Average Molecular Weight

94.133

Monoisotopic Molecular Weight

94.008850126

IUPAC Name

methanesulfonylmethane

Traditional Name

methylsulfonylmethane

CAS Registry Number

67-71-0

SMILES

CS(C)(=O)=O

InChI Identifier

InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3

InChI Key

HHVIBTZHLRERCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfonyls

Sub Class

Sulfones

Direct Parent

Sulfones

Alternative Parents

Substituents

Sulfone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfone (CHEBI:9349 )
a sulfone (CPD-10437 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Microbe:

Afipia

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Biological role:

Molecular messenger:

Signaling molecule

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	109 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.41	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	55.8 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-1.3	ChemAxon
logS	-0.23	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.53 m³·mol⁻¹	ChemAxon
Polarizability	8.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-3e72edc8bd8e168298a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-9000000000-9896ec507f104ada81f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-aad0ad2e46e9a93df295	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-8cb5ee5ae152833c1e84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-fb26633c75e592809868	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-3a6db80e12370ab204a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9000000000-c5c35fbdd4193d0ece0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-c0a7fe921fa7e601fb70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-113ab821ffdae95a6086	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fu-9000000000-2ef5cb880f6a43bd9df3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Brain
Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.5-16.1 uM	Adult (>18 years old)	Both	Normal	15996001	details
Blood	Detected and Quantified	8.8 +/- 7.3 uM	Adult (>18 years old)	Not Specified	Normal	15996001	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.0 +/- 1.0 uM	Adult (>18 years old)	Both	Normal	18502700	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.3 +/- 6.2 uM	Adult (>18 years old)	Not Specified	Normal	15996001	details
Saliva	Detected and Quantified	13.53 +/- 5.14 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	8.0 (1.3-49.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	4.6 (2.5-7.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	11.371 +/- 7.16 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	37.5 - 42.5 uM	Adult (>18 years old)	Both	Methionine adenosyltransferase (MAT) I/III deficiency	15996001	details
Blood	Detected and Quantified	5.06 (3.56) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	4.78 (2.73) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	574.0 uM	Adult (>18 years old)	Both	Methionine adenosyltransferase (MAT) I/III deficiency	15996001	details
Urine	Detected and Quantified	10.047 +/- 14.963 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Methionine adenosyltransferase deficiency
Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. [PubMed:15996001 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

250850 (Methionine adenosyltransferase deficiency)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006725

KNApSAcK ID

Not Available

Chemspider ID

5978

KEGG Compound ID

C11142

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylsulfonylmethane

METLIN ID

7236

PubChem Compound

6213

PDB ID

Not Available

ChEBI ID

9349

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Douglas, Thomas B. Heats of formation of liquid methyl suffoxide and crystalline methyl sulfone at 18° Journal of the American Chemical Society (1946), 68 1072-6.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Rogovin JL: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2002 Mar 28;129(3):263; author reply 265. [PubMed:11888710 ]
Rose SE, Chalk JB, Galloway GJ, Doddrell DM: Detection of dimethyl sulfone in the human brain by in vivo proton magnetic resonance spectroscopy. Magn Reson Imaging. 2000 Jan;18(1):95-8. [PubMed:10642107 ]
Lin A, Nguy CH, Shic F, Ross BD: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2001 Sep 15;123(2-3):169-77. [PubMed:11641045 ]
Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. [PubMed:15996001 ]

Showing metabocard for Dimethyl sulfone (HMDB0004983)

Structure for HMDB0004983 (Dimethyl sulfone)