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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015449
Secondary Accession Numbers
  • HMDB15449
Metabolite Identification
Common NameIohexol
DescriptionIohexol is only found in individuals that have used or taken this drug. It is an effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality. [PubChem]Organic iodine compounds block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intrathecal administration into the subarachnoid space, diffusion of iohexol in the CSF allows the visualization of the subarachnoid spaces of the head and spinal canal. After intravascular administration, iohexol makes opaque those vessels in its path of flow, allowing visualization of the internal structures until significant hemodilution occurs.
Structure
Data?1582753298
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 Weight821.1379
Monoisotopic Molecular Weight820.880309705
IUPAC NameN1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
Traditional Nameiohexol
CAS Registry Number66108-95-0
SMILES
CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.8 g/LNot Available
LogP-3.05HANSCH,C & LEO,AJ (1985)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+222.98230932474
DeepCCS[M-H]-220.62430932474
DeepCCS[M-2H]-253.83630932474
DeepCCS[M+Na]+229.07530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IohexolCC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I6273.9Standard polar33892256
IohexolCC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I3655.3Standard non polar33892256
IohexolCC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I5531.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Iohexol,1TMS,isomer #1CC(=O)N(CC(CO)O[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I4653.9Semi standard non polar33892256
Iohexol,1TMS,isomer #1CC(=O)N(CC(CO)O[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I4077.4Standard non polar33892256
Iohexol,1TMS,isomer #1CC(=O)N(CC(CO)O[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I6556.8Standard polar33892256
Iohexol,1TMS,isomer #2CC(=O)N(CC(O)CO[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I4665.6Semi standard non polar33892256
Iohexol,1TMS,isomer #2CC(=O)N(CC(O)CO[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I4092.8Standard non polar33892256
Iohexol,1TMS,isomer #2CC(=O)N(CC(O)CO[Si](C)(C)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I6514.0Standard polar33892256
Iohexol,1TMS,isomer #5CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(CC(O)CO)[Si](C)(C)C)=C1I4625.1Semi standard non polar33892256
Iohexol,1TMS,isomer #5CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(CC(O)CO)[Si](C)(C)C)=C1I4089.3Standard non polar33892256
Iohexol,1TMS,isomer #5CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(CC(O)CO)[Si](C)(C)C)=C1I6660.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Iohexol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iohexol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0udi-0000000090-ec4e884f5d1e3e37a84f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0udi-0020002090-d8ff0c2813768e3cf0122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-00dj-0009850000-7a1ca449a56d19c39ea82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0fk9-0009120000-a8c863a64d387cfd461a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0kmi-0496000000-bff588cc0e98918355e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-05fu-0492000000-4a9469f17183d2f9f2912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0udi-0020003090-7423fd2df7e59f0f78ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0fka-0008951000-ea0d52cf6d356a7f35902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0fk9-0029120000-e5ff4d33e064ff47ff492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0kmi-0395000000-775d49075e4ad66be1192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-05i1-0492000000-1a8b12a2e372f5b00ca12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOFsplash10-0udi-0000000090-262fc3f19d84427424082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 30V, Positive-QTOFsplash10-0fka-0008951000-ea0d52cf6d356a7f35902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 15V, Positive-QTOFsplash10-0udi-0020003090-7423fd2df7e59f0f78ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 15V, Positive-QTOFsplash10-0udi-0020002090-d8ff0c2813768e3cf0122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 30V, Positive-QTOFsplash10-00dj-0009850000-7a1ca449a56d19c39ea82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 35V, Positive-QTOFsplash10-0udi-0000000090-1c4236fb036bdcb8919d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 35V, Positive-QTOFsplash10-0udi-0000000090-d2b2317c9e97d635bc752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Iohexol 40V, Positive-QTOFsplash10-0udi-0000000090-292177f12e5c86adf9172021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 10V, Positive-QTOFsplash10-0fk9-3000000690-15559409f183bedfd23b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 20V, Positive-QTOFsplash10-0h2o-5000001920-b963e6f65dbbef4c7fc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 40V, Positive-QTOFsplash10-00dm-6000019700-febd0dbaea02e66b12d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 10V, Negative-QTOFsplash10-014i-0000000590-85bff61bbfe55d6063c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 20V, Negative-QTOFsplash10-0w5a-3700000920-a293fa4682474e7a56a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iohexol 40V, Negative-QTOFsplash10-0fvl-7500007900-33f05d012fa989b6149f2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01362 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01362 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01362
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3599
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIohexol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID31709
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. [PubMed:3882609 ]
  2. Kawada TK: Iohexol and iopamidol: second-generation nonionic radiographic contrast media. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):525-9. [PubMed:3896713 ]