Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: isethionate

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

Superclasses: an organosulfur compound an organosulfonate an aliphatic sulfonate an alkanesulfonate

Summary:
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

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

InChIKey: InChIKey=SUMDYPCJJOFFON-UHFFFAOYSA-M

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 oxidized electron acceptor + oxygen + 4 H+ → sulfoacetaldehyde + a reduced electron acceptor + 2 H2O

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

two-component alkanesulfonate monooxygenase :
an alkanesulfonate + 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+

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


References

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


Report Errors or Provide Feedback
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 18.5 on Sun Nov 23, 2014, biocyc13.