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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:11 UTC
Secondary Accession Numbers
  • HMDB03309
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 ).
3-Indolyl hydrogen sulfateChEBI
3-Indolyl sulfateChEBI
3-Indoxyl sulfateChEBI
3-Indoxylsulfuric acidChEBI
indol-3-yl Hydrogen sulfateChEBI
indol-3-yl SulfateChEBI
indol-3-yl SulphateChEBI
Indoxyl sulfic acidChEBI
Indoxyl sulphateChEBI
Indoxylsulfuric acidChEBI
3-Indolyl hydrogen sulfuric acidGenerator
3-Indolyl hydrogen sulphateGenerator
3-Indolyl hydrogen sulphuric acidGenerator
Indoxyl sulfuric acidGenerator
Indoxyl 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-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
Indoxylsulphuric acidGenerator
1H-indol-3-yl Hydrogen sulfateHMDB
1H-indol-3-yl Hydrogen sulphateHMDB
Chemical FormulaC8H7NO4S
Average Molecular Weight213.21
Monoisotopic Molecular Weight213.009578407
IUPAC Name1H-indol-3-yloxidanesulfonic acid
Traditional Name3-sulfooxy-1H-indole
CAS Registry Number487-94-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
  • Indole
  • Sulfuric acid monoester
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.79 mg/mLALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.39 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.12 m3·mol-1ChemAxon
Polarizability19.37 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0fk9-1890000000-1ccefb12c0ecb58cd51fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0bu0-1940000000-990f3edaa0f09b455534View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0790000000-bc45c54af242dc72b9dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-2090000000-53c9050daddd26dc4b7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9200000000-2fa7a5fde4214df01ed2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-9000000000-c9eec4c054ae464098edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-3cb045bd6bc8f7f8c2b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-6290000000-83be1b2526f53131a6ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9400000000-13c9487183bfd123ac3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9100000000-cf4b2fd59d8e983cb538View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-d0f51465d6c4ede36ea4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01si-9350000000-7227b62421572ea4e5f7View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Muscle
  • Prostate
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified14.0 +/- 4.2 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
BloodDetected and Quantified2.49 +/- 1.36 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified129.0 (45.0-191.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified19.74 +/- 5.26 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
UrineDetected and Quantified17.76 +/- 6.58 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
UrineDetected and Quantified1.41-51.64 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
UrineDetected and Quantified41.689 +/- 44.971 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected and Quantified18.98 umol/mmol creatinineAdult (>18 years old)Male
    • Shaykhutdinov RA,...
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
UrineDetected and Quantified420 +/- 210 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Abnormal Concentrations
BloodDetected and Quantified21.11 +/- 12.20 uMAdult (>18 years old)Bothuremia details
UrineDetected and Quantified36.932 +/- 21.826 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022179
KNApSAcK IDNot Available
Chemspider ID9840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndican
NuGOwiki LinkHMDB00682
Metagene LinkHMDB00682
PubChem Compound10258
ChEBI ID43355
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. [8257730 ]
  2. 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. [19212411 ]
  3. 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. [6321058 ]
  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. [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. [14681860 ]
  6. Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [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. [17403109 ]