MetaCyc Compound: isethionate

Synonyms: isethionic acid, 2-hydroxyethanesulfonate, 2-hydroxyethanesulfonic acid, 2-hydroxyethane-1-sulfonic acid

Superclasses: an organosulfur compound a sulfonate an aliphatic sulfonate an alkylsulfonate

Isethionate (2-hydroxyethanesulfonate) is found at high concentrations in several terrestrial and marine environments. Concentration of about 200 mM were measured in red algae [Barrow93, Hellio04] and the squid giant axon [Koechlin54]. An extremely high concentration of 2M is found in the sticky secretion that covers the silk orb web of an araneoid spider [Townley06]. Lower concentrations of isethionate are found in mammalian tissues [Kumpulainen82] and urine [Jacobsen67].

Chemical Formula: C2H5O4S

Molecular Weight: 125.12 Daltons

Monoisotopic Molecular Weight: 125.998679371 Daltons

isethionate compound structure

SMILES: C(CO)S(=O)(=O)[O-]

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


Unification Links: CAS:107-36-8 , ChEBI:61904 , ChemSpider:3176358 , HMDB:HMDB03903 , IAF1260:45154 , KEGG:C05123 , PubChem:3955599

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -85.61646 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

isethionate degradation :
isethionate + an unknown reduced electron acceptor + oxygen → sulfoacetaldehyde + an unknown oxidized electron acceptor + 2 H2O

Not in pathways:
isethionate + FMNH2 + oxygen → glycolaldehyde + sulfite + FMN + H2O + 2 H+

two-component alkanesulfonate monooxygenase :
an alkylsulfonate + FMNH2 + oxygen → an aldehyde + sulfite + FMN + H2O + 2 H+

Reactions known to produce the compound:

sulfoacetaldehyde degradation III :
isethionate + NADP+ ← sulfoacetaldehyde + NADPH + H+

In Transport reactions:
ATP + an aliphatic sulfonate[periplasmic space] + H2O → an aliphatic sulfonate[cytosol] + ADP + phosphate + H+

Revised 09-Feb-2011 by Caspi R , SRI International


Barrow93: Barrow, K. D., King, R. J., Karsten, U. (1993). "Isethionic acid from the marine red alga Ceramium flaccidum." Phytochemistry 34(5):1429-1430.

Hellio04: Hellio C, Simon-Colin C, Clare AS, Deslandes E (2004). "Isethionic acid and floridoside isolated from the red alga, Grateloupia turuturu, inhibit settlement of Balanus amphitrite cyprid larvae." Biofouling 20(3);139-45. PMID: 15545063

Jacobsen67: Jacobsen JG, Collins LL, Smith LH (1967). "Urinary excretion of isethionic acid in man." Nature 214(5094);1247-8. PMID: 6066118

Koechlin54: Koechlin BA (1954). "The isolation and identification of the major anion fraction of the axoplasm of squid giant nerve fibers." Proc Natl Acad Sci U S A 40(2);60-2. PMID: 16589435

Kumpulainen82: Kumpulainen E, Pesonen I, Lahdesmaki P (1982). "Exchange of isethionate between blood and tissues in adult and 7-day-old mice." Acta Physiol Scand 114(3);419-23. PMID: 6291329

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Townley06: Townley MA, Tillinghast EK, Neefus CD (2006). "Changes in composition of spider orb web sticky droplets with starvation and web removal, and synthesis of sticky droplet compounds." J Exp Biol 209(Pt 8);1463-86. PMID: 16574806

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Fri Mar 27, 2015, biocyc14.