Record Information
Version2.0
Creation Date2012-07-30 14:55:22 -0600
Update Date2015-09-17 15:42:08 -0600
Secondary Accession Numbers
  • ECMDB21344
Identification
Name:Methanesulfonate
DescriptionMesylate esters are a group of organic compounds that share a common functional group with the general structure CH3SO2O-R, abbreviated MsO-R, where R is an organic substituent. Mesylate is considered an excellent leaving group in nucleophilic substitution reactions.
Structure
Thumb
Synonyms:
  • Camostat mesilate
  • Camostat mesilic acid
  • Camostat mesylate
  • Camostat mesylic acid
  • Camostat monomethanesulfonate
  • Camostat monomethanesulfonic acid
  • Camostat monomethanesulphonate
  • Camostat monomethanesulphonic acid
  • Methanesulfonate
  • Methanesulfonic acid
  • Methanesulphonate
  • Methanesulphonic acid
  • Methylsulfonate
  • Methylsulfonic acid
  • Methylsulphonate
  • Methylsulphonic acid
  • MSA
Chemical Formula:CH3O3S
Weight:Average: 95.09
Monoisotopic: 94.980838711
InChI Key:AFVFQIVMOAPDHO-UHFFFAOYSA-M
InChI:InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)/p-1
CAS number:59721-29-8
IUPAC Name:4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate
Traditional IUPAC Name:camostat
SMILES:CS([O-])(=O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Guanidinobenzoic acid or derivatives
  • Benzoate ester
  • Phenol ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Guanidine
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP1.88ALOGPS
logP1.51ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)19.54ChemAxon
pKa (Strongest Basic)8.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area134.81 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.77 m³·mol⁻¹ChemAxon
Polarizability41.93 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-5980000000-dd72b99dcff9f0731fd9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4m-0149000000-972d002a862b25b2b321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-1269000000-51375cd035822d5d10d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9520000000-ab5a53059418ed6b9cf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0m4k-1139000000-e50a3d2b9bc0b0821b8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vj-2394000000-7a259b5895322bf21836View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0017-7590000000-d8e2761e33757111c0c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0339000000-d43f0e2ae28e1f28adb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-1954000000-d59d964dd758a5bb75aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-5900000000-fa5f799fa0f85a1118dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0149000000-f00bf55878d65b180cbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-1293000000-44d77c9b556e13cdd92aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ka-2910000000-15aa9f36000f3fe2a97cView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID25224
HMDB IDHMDB0249575
Pubchem Compound ID5284360
Kegg IDC11145
ChemSpider ID2440
WikipediaMethanesulfonate
BioCyc IDCPD-3746
EcoCyc IDCPD-3746

Enzymes

General function:
Involved in FMN reductase activity
Specific function:
Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
Gene Name:
ssuE
Uniprot ID:
P80644
Molecular weight:
21253
Reactions
FMNH(2) + NADP(+) = FMN + NADPH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925
General function:
Involved in sulfur compound metabolic process
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Putative binding protein
Gene Name:
ssuA
Uniprot ID:
P75853
Molecular weight:
34557
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Uniprot ID:
P0AAI1
Molecular weight:
27738

Transporters

General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925
General function:
Involved in sulfur compound metabolic process
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Putative binding protein
Gene Name:
ssuA
Uniprot ID:
P75853
Molecular weight:
34557
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Uniprot ID:
P0AAI1
Molecular weight:
27738
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368