Record Information
Version1.0
Creation date2011-09-21 00:09:41 UTC
Update date2015-10-09 22:30:37 UTC
Primary IDFDB022179
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number487-94-5
Structure
Thumb
Synonyms
SynonymSource
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
Indol-3-olhmdb
Indol-3-yl sulfatehmdb
indol-3-yl sulphatehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
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
Chemical FormulaC8H7NO4S
IUPAC name(1H-indol-3-yl)oxidanesulfonic acid
InChI IdentifierInChI=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
Isomeric SMILESOS(=O)(=O)OC1=CNC2=CC=CC=C12
Average Molecular Weight213.21
Monoisotopic Molecular Weight213.009578407
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fk9-1890000000-1ccefb12c0ecb58cd51fJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0bu0-1940000000-990f3edaa0f09b455534JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0790000000-bc45c54af242dc72b9dbJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-1920000000-61513ebc6b785c807016JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2090000000-53c9050daddd26dc4b7fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9200000000-2fa7a5fde4214df01ed2JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-c9eec4c054ae464098edJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-3cb045bd6bc8f7f8c2b0JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-6290000000-83be1b2526f53131a6ebJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9400000000-13c9487183bfd123ac3bJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9100000000-cf4b2fd59d8e983cb538JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-d0f51465d6c4ede36ea4JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01si-9350000000-7227b62421572ea4e5f7JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-8fc92d1f6e32863121d3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03e9-6290000000-b9b7292552ce2dcfccffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9400000000-7348f8347e517b6e1de2JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9100000000-e9a190cf92fcef264150JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-d0f51465d6c4ede36ea4JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01si-9350000000-7227b62421572ea4e5f7JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-d5c9e813f433f6a44f0fJSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-6917b03dbdcafea36737JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0930000000-6cb7fcdb7b15b9a9e80aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-3b57e4454fb97f3e1a1aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-bcbb5c8a331119233939JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0910000000-0d28f0b8a4ef10141bf2JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-a394015845114b618d01JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID9840
    ChEMBL IDCHEMBL1233636
    KEGG Compound IDNot Available
    Pubchem Compound ID10258
    Pubchem Substance IDNot Available
    ChEBI ID16700
    Phenol-Explorer IDNot Available
    DrugBank IDDB07992
    HMDB IDHMDB00682
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDIOS
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDIndican
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference