Record Information
Version1.0
Creation Date2016-07-13 19:44:51 UTC
Update Date2016-07-20 21:03:39 UTC
LmdbLMDB00213
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndoxyl sulfate
DescriptionIndoxyl sulfate is a dietary protein metabolite, and also the metabolite of the common amino acid tryptophan. Indoxyl sulfate is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress; in vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells, and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblst function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell. (PMID: 10681668 , 14681860 , 17471003 , 17403109 ).
Structure
Thumb
Synonyms
ValueSource
3-Indolyl hydrogen sulfateChEBI
3-Indolyl sulfateChEBI
3-Indoxyl sulfateChEBI
3-Indoxylsulfuric acidChEBI
IndicanChEBI
indol-3-yl Hydrogen sulfateChEBI
indol-3-yl SulfateChEBI
indol-3-yl SulphateChEBI
Indoxyl sulfic acidChEBI
Indoxyl sulphateChEBI
Indoxyl-3-sulphateChEBI
Indoxylsulfuric acidChEBI
3-Indolyl hydrogen sulfuric acidGenerator
3-Indolyl hydrogen sulphateGenerator
3-Indolyl hydrogen sulphuric acidGenerator
3-Indolyl sulfuric acidGenerator
3-Indolyl sulphateGenerator
3-Indolyl sulphuric acidGenerator
3-Indoxyl sulfuric acidGenerator
3-Indoxyl sulphateGenerator
3-Indoxyl sulphuric acidGenerator
3-IndoxylsulfateGenerator
3-IndoxylsulphateGenerator
3-Indoxylsulphuric acidGenerator
indol-3-yl Hydrogen sulfuric acidGenerator
indol-3-yl Hydrogen sulphateGenerator
indol-3-yl Hydrogen sulphuric acidGenerator
indol-3-yl Sulfuric acidGenerator
indol-3-yl Sulphuric acidGenerator
Indoxyl sulfuric acidGenerator
Indoxyl sulphuric acidGenerator
Indoxyl-3-sulfateGenerator
Indoxyl-3-sulfuric acidGenerator
Indoxyl-3-sulphuric acidGenerator
IndoxylsulfateGenerator
IndoxylsulphateGenerator
Indoxylsulphuric acidGenerator
1H-indol-3-yl Hydrogen sulfateHMDB
1H-indol-3-yl Hydrogen sulphateHMDB
indol-3-OlHMDB
Indican monosodium saltHMDB
Monopotassium salt, indicanHMDB
Monosodium salt, indicanHMDB
Sulfate, indoxylHMDB
Indican monopotassium saltHMDB
1H-indol-3-Ol hydrogen sulfate esterHMDB
3-Sulphooxy-1H-indoleHMDB
Indoxyl sulfateGenerator
Chemical FormulaC8H7NO4S
Average Molecular Weight213.21
Monoisotopic Molecular Weight213.009578407
IUPAC Name(1H-indol-3-yl)oxidanesulfonic acid
Traditional Name3-sulfooxy-1H-indole
CAS Registry Number487-94-5
SMILES
OS(=O)(=O)OC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)
InChI KeyBXFFHSIDQOFMLE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentArylsulfates
Alternative Parents
Substituents
  • Arylsulfate
  • Indole
  • Indole or derivatives
  • Substituted pyrrole
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.48ALOGPS
logP1.29ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.12 m³·mol⁻¹ChemAxon
Polarizability19.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fk9-1890000000-1ccefb12c0ecb58cd51fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0bu0-1940000000-990f3edaa0f09b455534Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0790000000-bc45c54af242dc72b9dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-1920000000-61513ebc6b785c807016Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2090000000-53c9050daddd26dc4b7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9200000000-2fa7a5fde4214df01ed2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-c9eec4c054ae464098edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-3cb045bd6bc8f7f8c2b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-6290000000-83be1b2526f53131a6ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9400000000-13c9487183bfd123ac3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9100000000-cf4b2fd59d8e983cb538Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-d0f51465d6c4ede36ea4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01si-9350000000-7227b62421572ea4e5f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-8fc92d1f6e32863121d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03e9-6290000000-b9b7292552ce2dcfccffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9400000000-7348f8347e517b6e1de2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9100000000-e9a190cf92fcef264150Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-d0f51465d6c4ede36ea4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01si-9350000000-7227b62421572ea4e5f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-d5c9e813f433f6a44f0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2ada8a129d47cf18cf2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03e9-8190000000-b7fa2468dad04ce9cf7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0059-9300000000-4ef26d7f6ffd8a0309a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-bcbb5c8a331119233939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0910000000-0d28f0b8a4ef10141bf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-a394015845114b618d01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-6917b03dbdcafea36737Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0930000000-6cb7fcdb7b15b9a9e80aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-3b57e4454fb97f3e1a1aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
DrugBank IDDB07992
HMDB IDHMDB0000682
FooDB IDFDB022179
Phenol Explorer IDNot Available
KNApSAcK IDC00052323
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID524
PDB IDNot Available
Wikipedia LinkIndoxyl sulfate
Chemspider ID9840
ChEBI ID43355
PubChem Compound ID10258
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aoyama I, Miyazaki T, Niwa T: Preventive effects of an oral sorbent on nephropathy in rats. Miner Electrolyte Metab. 1999 Jul-Dec;25(4-6):365-72. [10681668 ]
  2. Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. [14681860 ]
  3. Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [17471003 ]
  4. Dou L, Jourde-Chiche N, Faure V, Cerini C, Berland Y, Dignat-George F, Brunet P: The uremic solute indoxyl sulfate induces oxidative stress in endothelial cells. J Thromb Haemost. 2007 Jun;5(6):1302-8. [17403109 ]