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Ethanesulfonate (M2MDB001731)

Record Information
Version2.0
Creation Date2012-07-30 14:55:20 -0600
Update Date2015-06-03 17:21:10 -0600
Secondary Accession Numbers
  • ECMDB21330
Identification
Name:Ethanesulfonate
DescriptionEthanesulfonate is a member of the chemical class known as Depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually -amino and -hydroxy acids), commonly but not necessarily regularly alternating. It is also called Coenzyme M. Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of methanogens. The coenzyme is an anion with the formula HSCH2CH2SO_3. It is named 2-mercaptoethanesulfonate and abbreviated HS
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1-THIOETHANEsulfonate
  • 1-THIOETHANESULFONIC ACID
  • 1-THIOETHANEsulphonate
  • 1-THIOETHANEsulphonic acid
  • 2-Mercaptoethanesulfonate
  • 2-Mercaptoethanesulfonic acid
  • 2-Mercaptoethanesulphonate
  • 2-Mercaptoethanesulphonic acid
  • 2-Mercaptoethylsulfonate
  • 2-Mercaptoethylsulfonic acid
  • 2-Mercaptoethylsulphonate
  • 2-Mercaptoethylsulphonic acid
  • 2-Sulfanylethanesulfonate
  • 2-Sulfanylethanesulfonic acid
  • 2-Sulfanylethylsulfonate
  • 2-Sulfanylethylsulfonic acid
  • 2-Sulphanylethanesulphonate
  • 2-Sulphanylethanesulphonic acid
  • 2-Sulphanylethylsulphonate
  • 2-Sulphanylethylsulphonic acid
  • b-Mercaptoethanesulfonate
  • b-Mercaptoethanesulfonic acid
  • b-Mercaptoethanesulphonate
  • b-Mercaptoethanesulphonic acid
  • Beta-Mercaptoethanesulfonate
  • Beta-Mercaptoethanesulfonic acid
  • Beta-Mercaptoethanesulphonate
  • Beta-Mercaptoethanesulphonic acid
  • Camostat mesilate
  • Camostat mesilic acid
  • Camostat mesylate
  • Camostat mesylic acid
  • Camostat monomethanesulfonate
  • Camostat monomethanesulfonic acid
  • Camostat monomethanesulphonate
  • Camostat monomethanesulphonic acid
  • Coenzima M
  • Coenzym M
  • Coenzyme M
  • CoM
  • Ethanesulfonic acid
  • Ethanesulphonate
  • Ethanesulphonic acid
  • HS-CoM
  • Reduced coenzyme M
  • Reduced CoM
  • β-Mercaptoethanesulfonate
  • β-Mercaptoethanesulfonic acid
  • β-Mercaptoethanesulphonate
  • β-Mercaptoethanesulphonic acid
Chemical Formula:C20H22N4O5
Weight:Average: 398.4125
Monoisotopic: 398.159019834
InChI Key:XASIMHXSUQUHLV-UHFFFAOYSA-N
InChI:InChI=1S/C20H22N4O5/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22/h3-10H,11-12H2,1-2H3,(H4,21,22,23)
CAS number:59721-29-8
IUPAC Name:4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate
Traditional IUPAC Name:camostat
SMILES:CN(C)C(=O)COC(=O)CC1=CC=C(OC(=O)C2=CC=C(NC(N)=N)C=C2)C=C1
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:
Adenosine triphosphate + Water + Ethanesulfonate > ADP + Ethanesulfonate + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Ethanesulfonate > ADP + Ethanesulfonate + Hydrogen ion + Phosphate
Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
SMPDB Pathways:Not Available
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, 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
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
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
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17905
HMDB IDHMDB0249575
Pubchem Compound ID5284360
Kegg IDNot Available
ChemSpider ID2440
Wikipedia IDCamostat
BioCyc IDCPD-10434
EcoCyc IDCPD-10434

Enzymes

Protein Details
1. Alkanesulfonate monooxygenase
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.
Protein Details
2. Putative aliphatic sulfonates transport permease protein ssuC
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
Protein Details
3. Putative aliphatic sulfonates-binding protein
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
Protein Details
4. Aliphatic sulfonates import ATP-binding protein SsuB
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

Protein Details
1. Putative aliphatic sulfonates transport permease protein ssuC
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
Protein Details
2. Putative aliphatic sulfonates-binding protein
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
Protein Details
3. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
4. Outer membrane pore protein E
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
Protein Details
5. Outer membrane protein F
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
Protein Details
6. Aliphatic sulfonates import ATP-binding protein SsuB
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
Protein Details
7. Outer membrane protein C
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