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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:29 UTC
HMDB IDHMDB0000682
Secondary Accession Numbers
  • HMDB0003309
  • HMDB00682
  • HMDB03309
Metabolite Identification
Common NameIndoxyl sulfate
DescriptionIndoxyl sulfate is a dietary protein metabolite and also a metabolite of the common amino acid tryptophan. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). It 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 osteoblast 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 ). Indoxyl sulfate is a microbial metabolite found in Escherichia (PMID: 19946322 ).
Structure
Data?1582752149
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
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
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
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Muscle
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.0 +/- 4.2 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified2.49 +/- 1.36 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified129.0 (45.0-191.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified19.74 +/- 5.26 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified17.76 +/- 6.58 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.41-51.64 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified41.689 +/- 44.971 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified18.98 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified>0.658 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified22.4 (6.0-64.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified420 +/- 210 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified21.11 +/- 12.20 uMAdult (>18 years old)Bothuremia details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified36.932 +/- 21.826 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB07992
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022179
KNApSAcK IDNot Available
Chemspider ID9840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndoxyl sulfate
METLIN ID524
PubChem Compound10258
PDB IDNot Available
ChEBI ID43355
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceRobertson, Alexander. Synthesis of glucosides. I. Synthesis of indican. Journal of the Chemical Society (1927), 1937-43.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
  2. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
  3. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  4. 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. [PubMed:10681668 ]
  5. Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. [PubMed:14681860 ]
  6. Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [PubMed:17471003 ]
  7. 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. [PubMed:17403109 ]
  8. Evenepoel P, Meijers BK, Bammens BR, Verbeke K: Uremic toxins originating from colonic microbial metabolism. Kidney Int Suppl. 2009 Dec;(114):S12-9. doi: 10.1038/ki.2009.402. [PubMed:19946322 ]
  9. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]