Iohexol (CED0003166)

Record Information
Version1.0
Creation Date2016-05-22 03:41:59 UTC
Update Date2026-08-20 03:59:49 UTC
Accession NumberCHEM016736
Identification
Common NameIohexol
ClassSmall Molecule
Description
Iohexol is an organic compound with the chemical formula C19H26I3N3O9. Iohexol belongs to the anilides, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 821.14 g/mol, Iohexol is a heavy molecule. This substance has been identified in or released from 29 recorded sources across multiple sectors. Within aquatic systems and sediments, it is found in freshwater, seawater, surface water, and groundwater. It is also present in drinking water and water supply sources, including tap water, bottled water, and desalinated water. In the sector of wastewater, sanitation, and biosolids, it is recorded in wastewater, unspecified wastewater, industrial wastewater, mine wastewater, and wastewater treatment effluent. Iohexol is associated with electrical and electronic equipment, specifically X ray tubes, electric hearing aids, conductive bodies characterized by conductive materials, and electrically stimulated smoking devices. Additionally, it is found in household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, tobacco smoke filters, and non electric simulated smoking devices, as well as in appliances and HVAC refrigerants, including water heaters and water coolers. Exposure routes for Iohexol are diverse. These include intravenous, intravascular, and intrathecal administration, as well as oral, rectal, and inhalation routes. Other recorded routes of exposure include epidural, intracaudal, intralesional, intramuscular, intrasynovial, subarachnoid, perineural, infiltration, soft tissue, and topical application or touch.
Contaminant Type
  • Human Neurotoxin
  • PMT
Chemical Structure
Synonyms
ValueSource
IohexolumChEBI
N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamideChEBI
OmnipaqueKegg
Compound 545MeSH, HMDB
Iohexol 350MeSH, HMDB
ExypaqueMeSH, HMDB
NycodenzMeSH, HMDB
Iohexol injectionKEGG, HMDB
Chemical FormulaC19H26I3N3O9
Average Molecular Mass821.138 g/mol
Monoisotopic Mass820.880 g/mol
CAS Registry Number66108-95-0
IUPAC NameN1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
Traditional Nameiohexol
SMILESCC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I
InChI IdentifierInChI=1S/C19H26I3N3O9/c1-8(29)25(4-11(32)7-28)17-15(21)12(18(33)23-2-9(30)5-26)14(20)13(16(17)22)19(34)24-3-10(31)6-27/h9-11,26-28,30-32H,2-7H2,1H3,(H,23,33)(H,24,34)
InChI KeyNTHXOOBQLCIOLC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-haloacetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group, which is in turn ortho-substituted with a halogen atom.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentO-haloacetanilides
Alternative Parents
Substituents
  • O-haloacetanilide
  • P-haloacetanilide
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Acetamide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Alcohol
  • Organoiodide
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.8 g/LALOGPS
logP-2.8ALOGPS
logP-2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area199.89 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity148.84 m³·mol⁻¹ChemAxon
Polarizability60.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-ec4e884f5d1e3e37a84fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0020002090-d8ff0c2813768e3cf012Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-0009850000-7a1ca449a56d19c39ea8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-0009120000-a8c863a64d387cfd461aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0kmi-0496000000-bff588cc0e98918355e8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fu-0492000000-4a9469f17183d2f9f291Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0020003090-7423fd2df7e59f0f78eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fka-0008951000-ea0d52cf6d356a7f3590Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-0029120000-e5ff4d33e064ff47ff49Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0kmi-0395000000-775d49075e4ad66be119Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05i1-0492000000-1a8b12a2e372f5b00ca1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-262fc3f19d8442742408Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fka-0008951000-ea0d52cf6d356a7f3590Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0020003090-7423fd2df7e59f0f78eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0020002090-d8ff0c2813768e3cf012Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-0009850000-7a1ca449a56d19c39ea8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-1c4236fb036bdcb8919dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-d2b2317c9e97d635bc75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-292177f12e5c86adf917Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0000000090-b6617019a8ee2d6428f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fs-0009650000-35454e4852f06401eda7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-3000000690-15559409f183bedfd23bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h2o-5000001920-b963e6f65dbbef4c7fc5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dm-6000019700-febd0dbaea02e66b12d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000000590-85bff61bbfe55d6063c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w5a-3700000920-a293fa4682474e7a56a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fvl-7500007900-33f05d012fa989b6149fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0000000490-115c77fd0f9d5a32f271Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ir9-0000000920-3f7ef090090b7f1a1f97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2000004900-a983a5a7b57865252c5bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-0000009810-4e7bf762df55c74efd16Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0000004900-cf52a391108d74743765Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01bi-0000009200-54cf5ea9d68196f7869dNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)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
5034.0Log mg/kg[2800:9000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
417X-ray contrast media, iodinatedHealthcare, pharmaceuticals & veterinary productsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Dual specificity mitogen-activated protein kinase kinase 1 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 1Q02750HumansPredicted (SEA)2833.63
Dual specificity mitogen-activated protein kinase kinase 2 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 2P36507HumansPredicted (SEA)2352.91
Click to view 3D structureG protein-activated inward rectifier potassium channel 1P48549HumansPredicted (SEA)15.9591
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)5807.32
Click to view 3D structureIsoleucine--tRNA ligase, mitochondrialQ9NSE4HumansPredicted (SEA)161.304
Dual specificity mitogen-activated protein kinase kinase 5 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 5Q13163HumansPredicted (SEA)4890.49
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)7266.68
Integrin alpha-2 structureClick to view 3D structureIntegrin alpha-2P17301HumansPredicted (SEA)306.492
Integrin alpha-V structureClick to view 3D structureIntegrin alpha-VP06756HumansPredicted (SEA)496.756
Click to view 3D structureGlucose-6-phosphate isomeraseQ9N1E2Oryctolagus cuniculusPredicted (SEA)8.01847
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)7287.0
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)7565.78
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)7536.58
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)6300.03
Click to view 3D structureSialidase-1Q99519HumansPredicted (SEA)26.0016
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)7499.45
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)4128.5
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)6014.32
Click to view 3D structureProstaglandin F2-alpha receptorP43118Rattus norvegicusPredicted (SEA)1208.06
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)2046.19
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)1512.53
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)7561.03
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)7171.7
Serine/threonine-protein kinase B-raf structureClick to view 3D structureSerine/threonine-protein kinase B-rafP15056HumansPredicted (SEA)6957.23
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)7467.92
Concentrations
StatusValueUnitSample LocationReference
Detected and Quantified940ng/LBussigny-prés-Lausanne
Detected and QuantifiedVernier,Aïre
Detected and Quantified3000ng/LWinterthur
External Links
DrugBank IDDB01362
HMDB IDHMDB0257934
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIohexol
Chemspider ID3599
ChEBI ID31709
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15206581
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19359533
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23847035
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24516530
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24752695