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Showing metabocard for Iohexol (HMDB0015449)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:51:11 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
IohexolumChEBI
N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamideChEBI
Compound 545MeSH
Iohexol 350MeSH
OmnipaqueMeSH
ExypaqueMeSH
NycodenzMeSH
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
DescriptionThis compound 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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.8 g/LNot Available
LogP-3.05HANSCH,C & LEO,AJ (1985)
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0000000090-ec4e884f5d1e3e37a84fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0020002090-d8ff0c2813768e3cf012View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dj-0009850000-7a1ca449a56d19c39ea8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fk9-0009120000-a8c863a64d387cfd461aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0kmi-0496000000-bff588cc0e98918355e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fu-0492000000-4a9469f17183d2f9f291View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0020003090-7423fd2df7e59f0f78eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fka-0008951000-ea0d52cf6d356a7f3590View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fk9-0029120000-e5ff4d33e064ff47ff49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0kmi-0395000000-775d49075e4ad66be119View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05i1-0492000000-1a8b12a2e372f5b00ca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0000000090-262fc3f19d8442742408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3000000690-15559409f183bedfd23bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h2o-5000001920-b963e6f65dbbef4c7fc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-6000019700-febd0dbaea02e66b12d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000590-85bff61bbfe55d6063c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w5a-3700000920-a293fa4682474e7a56a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvl-7500007900-33f05d012fa989b6149fView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01362 details
UrineExpected but not Quantified Not 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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3599
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIohexol
METLIN IDNot Available
PubChem Compound3730
PDB IDNot Available
ChEBI ID31709
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 ]