ECMDB: Isethionic acid (ECMDB21233) (M2MDB001641)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)Transporters (10)XML

Proteins (17)

Record Information

Version

2.0

Creation Date

2012-07-30 14:55:03 -0600

Update Date

2015-09-13 15:15:31 -0600

Secondary Accession Numbers

ECMDB21233

Identification

Name:

Isethionic acid

Description

Isethionic acid (C2H6O4S) is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.; A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. The Escherichia coli ssuEADCB gene cluster is required for the utilization of alkanesulfonates (such as isethionic acid) as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2-Hydroxyethyl)sulfonate
(2-Hydroxyethyl)sulfonic acid
(2-Hydroxyethyl)sulphonate
(2-Hydroxyethyl)sulphonic acid
2-Hydroxy-Ethanesulfonate
2-Hydroxy-Ethanesulfonic acid
2-Hydroxy-Ethanesulphonate
2-Hydroxy-Ethanesulphonic acid
2-Hydroxyethane-1-sulfonate
2-Hydroxyethane-1-sulfonic acid
2-Hydroxyethane-1-sulphonate
2-Hydroxyethane-1-sulphonic acid
2-Hydroxyethanesulfonate
2-Hydroxyethanesulfonic acid
2-Hydroxyethanesulphonate
2-Hydroxyethanesulphonic acid
2-Hydroxyethylsulfonate
2-Hydroxyethylsulfonic acid
2-Hydroxyethylsulphonate
2-Hydroxyethylsulphonic acid
b-Hydroxyethanesulfonate
b-Hydroxyethanesulfonic acid
b-Hydroxyethanesulphonate
b-Hydroxyethanesulphonic acid
Beta-Hydroxyethanesulfonate
Beta-Hydroxyethanesulfonic acid
Beta-Hydroxyethanesulphonate
Beta-Hydroxyethanesulphonic acid
Ethanolsulfonate
Ethanolsulfonic acid
Ethanolsulphonate
Ethanolsulphonic acid
Hydroxyethylsulfonate
Hydroxyethylsulfonic acid
Hydroxyethylsulphonate
Hydroxyethylsulphonic acid
Isethionate
Isethionate sodium salt
Isethionic acid
Isethionic acid sodium salt
Kyselina isethionova
Potassium 2-hydroxyethanesulfonate
Potassium 2-hydroxyethanesulfonic acid
Potassium 2-hydroxyethanesulphonate
Potassium 2-hydroxyethanesulphonic acid
Potassium isethionate
Potassium isethionic acid
Sodium 2-hydroxyethanesulfonate
Sodium 2-hydroxyethanesulfonic acid
Sodium 2-hydroxyethanesulphonate
Sodium 2-hydroxyethanesulphonic acid
Sodium 2-hydroxyethyl sulfonate
Sodium 2-hydroxyethyl sulfonic acid
Sodium 2-hydroxyethyl sulphonate
Sodium 2-hydroxyethyl sulphonic acid
Sodium b-hydroxyethanesulfonate
Sodium b-hydroxyethanesulfonic acid
Sodium b-hydroxyethanesulphonate
Sodium b-hydroxyethanesulphonic acid
Sodium beta-hydroxyethanesulfonate
Sodium beta-hydroxyethanesulfonic acid
Sodium beta-hydroxyethanesulphonate
Sodium beta-hydroxyethanesulphonic acid
Sodium isethionate
Sodium isethionic acid
Sodium β-hydroxyethanesulfonate
Sodium β-hydroxyethanesulfonic acid
Sodium β-hydroxyethanesulphonate
Sodium β-hydroxyethanesulphonic acid
β-Hydroxyethanesulfonate
β-Hydroxyethanesulfonic acid
β-Hydroxyethanesulphonate
β-Hydroxyethanesulphonic acid

Chemical Formula:

C₂H₆O₄S

Weight:

Average: 126.132
Monoisotopic: 125.99867937

InChI Key:

SUMDYPCJJOFFON-UHFFFAOYSA-N

InChI:

InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)

CAS number:

107-36-8

IUPAC Name:

2-hydroxyethane-1-sulfonic acid

Traditional IUPAC Name:

sodium isethionate

SMILES:

OCCS(O)(=O)=O

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
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alkanesulfonic acid (CHEBI:1157 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

< 25 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	1000 mg/mL	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.95 m³·mol⁻¹	ChemAxon
Polarizability	10.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Water + Isethionic acid > ADP + Hydrogen ion + Isethionic acid + Phosphate
Adenosine triphosphate + Water + Isethionic acid > ADP + Hydrogen ion + Isethionic acid + Phosphate
FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000y-9100000000-91c2f22c70185fb5bafe	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9300000000-7f0eccc0156cbd7e5b23	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-b8df238a554a2725a4d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-6900000000-c72536efb4cfd09b2759	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-61473ee5b4612e7ca273	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-d85e73096201062faad2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ce44d57a4275daa8f563	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-981a5a0ee1738f6dd44b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-2bcca3d457e8f9197dda	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9300000000-620379edca41de90b8d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-f83dca3bb4164fb39fc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054k-8900000000-111dba10014f3cc5c403	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9300000000-5cc44eb483ce09d49510	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-6900000000-c1573e4b7aa0acf67018	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9600000000-894c171421adedc823bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-b8c542a1a77eb7a6a191	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-6b3e5cddcb84b830073f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-a6fb8cd4d3dc149be309	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-d1be4ea1280b92cdc8d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0059-5900000000-946a0582ff1c22137b29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-9200000000-1efad064df378bad76b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-2c4a3db8921d94d7f526	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kersten A, Althaus C, Seitz HM, Pfahl HG, Sundmacher R: [Bilateral microsporidial keratitis in an HIV-positive patient with AIDS stage infection] Klin Monatsbl Augenheilkd. 1998 Jun;212(6):476-9. Pubmed: 9715470

Synthesis Reference:

Chen, Zhiwen; Liao, Xiangxu; Qian, Weiqiang; et al. Process for preparation of hydroxyalkanesulfonic acids for plating solutions. Faming Zhuanli Shenqing Gongkai Shuomingshu (1990), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	1157
HMDB ID	HMDB03903
Pubchem Compound ID	7866
Kegg ID	C05123
ChemSpider ID	7578
Wikipedia	Isethionic_acid
BioCyc ID	CPD-3745
EcoCyc ID	CPD-3745

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. Taurine transport system permease protein tauC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: tauC
Uniprot ID:: Q47539
Molecular weight:: 29812

Protein Details

4. 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

5. Taurine import ATP-binding protein TauB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:: tauB
Uniprot ID:: Q47538
Molecular weight:: 28297

Reactions

ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).

Protein Details

6. Taurine-binding periplasmic protein

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine
Gene Name:: tauA
Uniprot ID:: Q47537
Molecular weight:: 34266

Protein Details

7. 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. Taurine transport system permease protein tauC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: tauC
Uniprot ID:: Q47539
Molecular weight:: 29812

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. 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

5. 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

6. 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

7. Taurine import ATP-binding protein TauB

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex TauABC involved in taurine import. Responsible for energy coupling to the transport system
Gene Name:: tauB
Uniprot ID:: Q47538
Molecular weight:: 28297

Reactions

ATP + H(2)O + taurine(Out) = ADP + phosphate + taurine(In).

Protein Details

8. Taurine-binding periplasmic protein

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for taurine
Gene Name:: tauA
Uniprot ID:: Q47537
Molecular weight:: 34266

Protein Details

9. 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

10. 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

Isethionic acid (ECMDB21233) (M2MDB001641)

Structure for #<Compound:0xada559d0>

Enzymes

Reactions

Reactions

Transporters

Reactions