Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB001743
Identification
Name: Methanesulfonate
Description:Mesylate 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
Average Molecular Weight: 95.09
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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).
Kingdom Organic compounds
Super ClassPhenylpropanoids and polyketides
Class Depsides and depsidones
Sub ClassNot Available
Direct Parent Depsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Guanidinobenzoic acid or derivatives
  • Phenylacetate
  • Phenol ester
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Guanidine
  • Carboxylic acid ester
  • Carboxamide group
  • Carboximidamide
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0626 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.77 m3·mol-1ChemAxon
Polarizability41.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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, 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
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID25224
HMDB IDNot Available
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
Locus Tag:
PA3446
Molecular weight:
21.5 kDa
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
Locus Tag:
PA3444
Molecular weight:
41.6 kDa
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
Locus Tag:
PA3443
Molecular weight:
28.5 kDa
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
Locus Tag:
PA3442
Molecular weight:
29.8 kDa

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
Locus Tag:
PA3443
Molecular weight:
28.5 kDa
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
Locus Tag:
PA3442
Molecular weight:
29.8 kDa