Indoxyl (CED0003128)

Record Information
Version1.0
Creation Date2016-05-26 05:56:43 UTC
Update Date2026-04-06 09:02:21 UTC
Accession NumberCHEM035636
Identification
Common NameIndoxyl
ClassSmall Molecule
Description
Indoxyl is an organic compound with the chemical formula C8H7NO and an average molecular weight of 133.15 g/mol. Indoxyl belongs to the hydroxyindoles, a subclass of indoles and derivatives within the organic compounds. This substance is found in or released from 19 recorded sources across multiple sectors. In the electrical and electronic equipment sector, it is associated with batteries, capacitors, cell phones, printed circuit boards, wires and cables, and five additional sources. Within the healthcare, pharmaceuticals and veterinary products sector, it is linked to medical devices. In the food, food processing and cookware sector, it is found in food packaging and the preparation of malt. It is also present in the textiles, leather and furnishings sector, specifically in carpets, rugs, and synthetic textiles. Additionally, the compound is found in lubricants within both the industrial manufacturing and chemical processing sector and the energy, oil and gas sector, as well as two other sectors. Recorded exposure routes for indoxyl include oral, inhalation, and touch.
Contaminant Type
  • PFAS
Chemical Structure
Synonyms
ValueSource
1H-indol-3-OlChEBI
Chemical FormulaC8H7NO
Average Molecular Mass133.147 g/mol
Monoisotopic Mass133.053 g/mol
CAS Registry Number480-93-3
IUPAC Name1H-indol-3-ol
Traditional Nameindoxyl
SMILESOC1=CNC2=CC=CC=C12
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-004i-3980000000-520b4525adaeb185fb13Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-004i-3980000000-520b4525adaeb185fb13Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0kai-1900000000-1c5e163741d871a2c138Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fl3-6910000000-0c8f4cb37b60dcecf8eaNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-e2d4dbd9b806b29ce214Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-9500000000-263e6cbbc9fbea4d1fe2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-601cd8ae4909db7a541aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-0276e7599b0c044e16caNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003r-8900000000-1a948ecd165e51423035Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-6900000000-e7a7e7fb048f732eb685Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-4900000000-e34a5c59b0cce2170e4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-271db1608159a875a61cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-e357308e88e379d8eb0bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-ce70e056e1f4cfdf3761Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-9beba85555a54c1f672eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kui-7900000000-c36b8119a51196a1f474Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-0d126f50596b5c4ae9ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-d5b63c4616a3ca6983c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-f4d199baa93fba2d315cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-ac524f6f858437766e2fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-1064492c92995ca99566Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9300000000-62b87115059cfc657adcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-a956a3a0009c6965897aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-7b07769eadb95204ac58Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-fea25d8ed304aa380484Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
887.0Log mg/kg[500:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
602MolluscicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)68.5073
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)54.728
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)64.537
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)93.2634
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)32.6188
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)47.7994
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)51.3805
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)14.7135
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)3.73676
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)28.415
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)83.3765
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)36.1999
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)199.294
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)45.3082
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)102.917
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)95.0539
5-hydroxytryptamine receptor 5A structureClick to view 3D structure5-hydroxytryptamine receptor 5AP47898HumansPredicted (SEA)31.8403
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)13.6236
Aryl hydrocarbon receptor structureClick to view 3D structureAryl hydrocarbon receptorP35869HumansPredicted (SEA)0.467095
Myeloperoxidase structureClick to view 3D structureMyeloperoxidaseP05164HumansPredicted (SEA)6.53933
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)197.503
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)45.3861
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)52.0811
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)110.157
5-hydroxytryptamine receptor 1E structureClick to view 3D structure5-hydroxytryptamine receptor 1EP28566HumansPredicted (SEA)20.3965
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0004094
FooDB IDFDB023310
Phenol Explorer IDNot Available
KNApSAcK IDC00025147
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7014
PDB IDNot Available
Wikipedia LinkIndoxyl
Chemspider ID45861
ChEBI ID17840
PubChem Compound ID50591
Kegg Compound IDC05658
YMDB IDNot Available
ECMDB IDM2MDB005948
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Stoppani, Andres O. M. Formation of indoxyl from nitro and amino derivatives of benzene. Revista de la Sociedad Argentina de Biologia (1943), 19 421-34.
2. 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.
3. 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.