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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-06-07 00:54:23 UTC

Update Date

2022-03-07 03:18:15 UTC

HMDB ID

HMDB0240280

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mesylate

Description

Mesylate, also known as methanesulfonate or mesylic acid, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Mesylate exists as a solid, soluble (in water), and an extremely strong acidic compound (based on its pKa). Mesylate is also a parent compound for other transformation products, including but not limited to, methanesulfonates, S-methyl methanethiosulfonate, and (Z)-11-methyl-N-(methylsulfonyl)dodec-2-enamide.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methansulfonsaeure	ChEBI
Methylsulfonic acid	ChEBI
Methanesulfonate	Kegg
Methansulphonsaeure	Generator
Methylsulfonate	Generator
Methylsulphonate	Generator
Methylsulphonic acid	Generator
Methanesulfonic acid	Generator
Methanesulphonate	Generator
Methanesulphonic acid	Generator
Mesylic acid	Generator

Chemical Formula

CH₄O₃S

Average Molecular Weight

96.106

Monoisotopic Molecular Weight

95.988114684

IUPAC Name

methanesulfonic acid

Traditional Name

methanesulfonic acid

CAS Registry Number

75-75-2

SMILES

CS(O)(=O)=O

InChI Identifier

InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)

InChI Key

AFVFQIVMOAPDHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic acids

Alternative Parents

Substituents

Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Methanesulfonate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:27376 )
alkanesulfonic acid (CHEBI:27376 )

Ontology

Not Available

Exogenous (HMDB: HMDB0240280)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-0.96	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	16.53 m³·mol⁻¹	ChemAxon
Polarizability	7.55 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	117.331	31661259
DarkChem	[M-H]-	108.953	31661259
DeepCCS	[M+H]+	127.301	30932474
DeepCCS	[M-H]-	124.503	30932474
DeepCCS	[M-2H]-	161.048	30932474
DeepCCS	[M+Na]+	135.516	30932474
AllCCS	[M+H]+	116.5	32859911
AllCCS	[M+H-H2O]+	112.2	32859911
AllCCS	[M+NH4]+	120.5	32859911
AllCCS	[M+Na]+	121.7	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	144.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	8.3442 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	925.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	350.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	260.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	281.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	686.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	580.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	736.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	608.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	289.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesylate	CS(O)(=O)=O	1926.6	Standard polar	33892256
Mesylate	CS(O)(=O)=O	700.8	Standard non polar	33892256
Mesylate	CS(O)(=O)=O	946.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mesylate,1TMS,isomer #1	C[Si](C)(C)OS(C)(=O)=O	1020.8	Semi standard non polar	33892256
Mesylate,1TMS,isomer #1	C[Si](C)(C)OS(C)(=O)=O	892.5	Standard non polar	33892256
Mesylate,1TMS,isomer #1	C[Si](C)(C)OS(C)(=O)=O	1397.6	Standard polar	33892256
Mesylate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(C)(=O)=O	1274.6	Semi standard non polar	33892256
Mesylate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(C)(=O)=O	1207.6	Standard non polar	33892256
Mesylate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(C)(=O)=O	1521.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mesylate GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate LC-ESI-QQ 10V, negative-QTOF	splash10-0002-9000000000-b0b5dd86e6d1a6de2171	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate LC-ESI-QQ 20V, negative-QTOF	splash10-000t-9000000000-2ee38f4f23a3f78e4e2a	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate LC-ESI-QQ 30V, negative-QTOF	splash10-001i-9000000000-f81ecc13632c4bbf047b	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate LC-ESI-QQ 40V, negative-QTOF	splash10-001i-9000000000-884a19f5db4e591e2bd5	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate LC-ESI-QQ 50V, negative-QTOF	splash10-001i-9000000000-a901585f4831b96565d2	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 4V, positive-QTOF	splash10-0002-9000000000-b7d4723b89df8c48ecec	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 5V, positive-QTOF	splash10-0002-9000000000-934bf853dc7107657ace	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 6V, positive-QTOF	splash10-0002-9000000000-dafaeba25475627e3a3e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 7V, positive-QTOF	splash10-002b-9000000000-ac2c0369a2e8961208e2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 8V, positive-QTOF	splash10-002b-9000000000-7486b361587e7f53ed50	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 9V, positive-QTOF	splash10-004j-9000000000-aadc7f742501b493df8d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 10V, positive-QTOF	splash10-004i-9000000000-00d2a96c874e0158a646	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 11V, positive-QTOF	splash10-004i-9000000000-97e140c69588e46d7c90	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 12V, positive-QTOF	splash10-004i-9000000000-9c9f2cbe42dd4f181327	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 13V, positive-QTOF	splash10-004i-9000000000-dc2e28378ca42df5a67d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 14V, positive-QTOF	splash10-004i-9000000000-107fbd2f4f6116fc025a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 15V, positive-QTOF	splash10-004i-9000000000-8566dc86c9429f7b9f69	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 16V, positive-QTOF	splash10-004i-9000000000-bee539c9f80053a39810	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesylate QqQ 17V, positive-QTOF	splash10-004i-9000000000-09c0bb99771ad74fc6f1	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 10V, Positive-QTOF	splash10-0002-9000000000-1b4796f40f88bb7e46d3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 20V, Positive-QTOF	splash10-0002-9000000000-c6a64728ed2079ff2055	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 40V, Positive-QTOF	splash10-0002-9000000000-c69360fc9c207fe9272c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 10V, Negative-QTOF	splash10-0006-9000000000-54a372ad2537ce986dfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 20V, Negative-QTOF	splash10-0006-9000000000-e7e9a7d67d5a8dd44695	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesylate 40V, Negative-QTOF	splash10-004i-9000000000-e0113f3b2a9f00039047	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB098394

KNApSAcK ID

Not Available

Chemspider ID

6155

KEGG Compound ID

C11145

BioCyc ID

CPD-3746

BiGG ID

Not Available

Wikipedia Link

Methanesulfonic_acid

METLIN ID

Not Available

PubChem Compound

6395

PDB ID

Not Available

ChEBI ID

27376

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1257511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Mesylate (HMDB0240280)

MOL for HMDB0240280 (Mesylate)

3D MOL for HMDB0240280 (Mesylate)

3D SDF for HMDB0240280 (Mesylate)

3D-SDF for HMDB0240280 (Mesylate)

PDB for HMDB0240280 (Mesylate)

3D PDB for HMDB0240280 (Mesylate)

SMILES for HMDB0240280 (Mesylate)

INCHI for HMDB0240280 (Mesylate)

Structure for HMDB0240280 (Mesylate)

3D Structure for HMDB0240280 (Mesylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra