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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:46:17 UTC
Update Date2021-09-07 16:45:36 UTC
HMDB IDHMDB0004094
Secondary Accession Numbers
  • HMDB04094
Metabolite Identification
Common NameIndoxyl
DescriptionIndoxyl, also known as 1H-indol-3-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl exists in all living organisms, ranging from bacteria to humans. Indoxyl is obtained from indican, which is a glycoside. Obermayer's reagent is a dilute solution FeCl3 in hydrochloric acid. The hydrolysis of indican yields β-D-glucose and indoxyl. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent such as atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl can be found in urine and is titrated with Obermayer's reagent.
Structure
Data?1582752298
Synonyms
ValueSource
1H-indol-3-OlChEBI
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name1H-indol-3-ol
Traditional Nameindoxyl
CAS Registry Number480-93-3
SMILES
OC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H
InChI KeyPCKPVGOLPKLUHR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.67 g/LALOGPS
logP1.29ALOGPS
logP1.77ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability13.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-157.45730932474
DeepCCS[M+Na]+132.530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndoxylOC1=CNC2=CC=CC=C122541.5Standard polar33892256
IndoxylOC1=CNC2=CC=CC=C121528.1Standard non polar33892256
IndoxylOC1=CNC2=CC=CC=C121508.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indoxyl,1TMS,isomer #1C[Si](C)(C)OC1=C[NH]C2=CC=CC=C121602.3Semi standard non polar33892256
Indoxyl,1TMS,isomer #2C[Si](C)(C)N1C=C(O)C2=CC=CC=C211706.1Semi standard non polar33892256
Indoxyl,2TMS,isomer #1C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C121782.5Semi standard non polar33892256
Indoxyl,2TMS,isomer #1C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C121708.8Standard non polar33892256
Indoxyl,2TMS,isomer #1C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C121710.5Standard polar33892256
Indoxyl,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C[NH]C2=CC=CC=C121869.4Semi standard non polar33892256
Indoxyl,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(O)C2=CC=CC=C211958.2Semi standard non polar33892256
Indoxyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122156.8Semi standard non polar33892256
Indoxyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122120.6Standard non polar33892256
Indoxyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122011.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indoxyl GC-MS (2 TMS)splash10-004i-3980000000-520b4525adaeb185fb132014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoxyl GC-MS (Non-derivatized)splash10-004i-3980000000-520b4525adaeb185fb132017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoxyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-1900000000-1c5e163741d871a2c1382017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoxyl GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-6910000000-0c8f4cb37b60dcecf8ea2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoxyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0900000000-e2d4dbd9b806b29ce2142012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-056r-9500000000-263e6cbbc9fbea4d1fe22012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-601cd8ae4909db7a541a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOFsplash10-001i-1900000000-0276e7599b0c044e16ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOFsplash10-003r-8900000000-1a948ecd165e514230352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOFsplash10-0a4i-6900000000-e7a7e7fb048f732eb6852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOFsplash10-001i-4900000000-e34a5c59b0cce2170e4f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOFsplash10-004i-9000000000-271db1608159a875a61c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOFsplash10-0006-9100000000-e357308e88e379d8eb0b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOFsplash10-001i-0900000000-ce70e056e1f4cfdf37612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOFsplash10-001i-0900000000-9beba85555a54c1f672e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOFsplash10-0kui-7900000000-c36b8119a51196a1f4742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOFsplash10-001i-0900000000-0d126f50596b5c4ae9ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOFsplash10-001i-0900000000-d5b63c4616a3ca6983c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOFsplash10-0udi-2900000000-f4d199baa93fba2d315c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOFsplash10-001i-0900000000-ac524f6f858437766e2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOFsplash10-001i-1900000000-1064492c92995ca995662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOFsplash10-004i-9300000000-62b87115059cfc657adc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOFsplash10-001i-0900000000-a956a3a0009c6965897a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOFsplash10-001i-0900000000-7b07769eadb95204ac582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOFsplash10-001i-0900000000-fea25d8ed304aa3804842021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023310
KNApSAcK IDC00025147
Chemspider ID45861
KEGG Compound IDC05658
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndoxyl
METLIN ID7014
PubChem Compound50591
PDB IDNot Available
ChEBI ID17840
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceStoppani, Andres O. M. Formation of indoxyl from nitro and amino derivatives of benzene. Revista de la Sociedad Argentina de Biologia (1943), 19 421-34.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Achtergael W, Michielsen D, Gorus FK, Gerlo E: Indoxyl sulphate and the purple urine bag syndrome: a case report. Acta Clin Belg. 2006 Jan-Feb;61(1):38-41. [PubMed:16673616 ]
  2. Delisle GJ, Ley A: Rapid detection of Escherichia coli in urine samples by a new chromogenic beta-glucuronidase assay. J Clin Microbiol. 1989 Apr;27(4):778-9. [PubMed:2656750 ]