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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:46:17 UTC
Update Date2019-01-11 19:17:55 UTC
HMDB IDHMDB0004094
Secondary Accession Numbers
  • HMDB04094
Metabolite Identification
Common NameIndoxyl
DescriptionIndigo dye is a product of the reaction of indoxyl by a mild oxidizing agent, eg. atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl is obtained from indican, which is a glycoside. The hydrolysis of indican yields beta-D-glucose and indoxyl.
Structure
Data?1547234275
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
DescriptionThis compound 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 Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-3980000000-520b4525adaeb185fb13View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-3980000000-520b4525adaeb185fb13View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-1900000000-1c5e163741d871a2c138View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-6910000000-0c8f4cb37b60dcecf8eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-e2d4dbd9b806b29ce214View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9500000000-263e6cbbc9fbea4d1fe2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-601cd8ae4909db7a541aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-ce70e056e1f4cfdf3761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-9beba85555a54c1f672eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kui-7900000000-c36b8119a51196a1f474View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-0d126f50596b5c4ae9ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-d5b63c4616a3ca6983c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2900000000-f4d199baa93fba2d315cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
FoodDB IDFDB023310
KNApSAcK IDNot Available
Chemspider ID45861
KEGG Compound IDC05658
BioCyc IDINDOXYL
BiGG IDNot Available
Wikipedia LinkIndoxyl
METLIN ID7014
PubChem Compound50591
PDB IDNot Available
ChEBI ID17840
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 ]