Human Metabolome Database: Showing metabocard for Iohexol (HMDB15449)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

3.6

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2017-03-02 21:33:57 UTC

HMDB ID

HMDB15449

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Iohexol

Description

Iohexol 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Iohexolum	ChEBI
N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide	ChEBI
Compound 545	MeSH
Iohexol 350	MeSH
Omnipaque	MeSH
Exypaque	MeSH
Nycodenz	MeSH

Chemical Formula

C₁₉H₂₆I₃N₃O₉

Average Molecular Weight

821.1379

Monoisotopic Molecular Weight

820.880309705

IUPAC Name

N1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide

Traditional Name

iohexol

CAS Registry Number

66108-95-0

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 Key

NTHXOOBQLCIOLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities 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.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

O-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

organoiodine compound (CHEBI:31709 )
benzenedicarboxamide (CHEBI:31709 )

Ontology

Status

Expected but not Quantified

Origin

Drug

Biofunction

Contrast Agents
Contrast Media

Application

Pharmaceutical

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	174 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.96e-01 g/L	Not Available
LogP	-3.05	HANSCH,C & LEO,AJ (1985)

Predicted Properties

Property	Value	Source
Water Solubility	0.8 mg/mL	ALOGPS
logP	-2.8	ALOGPS
logP	-2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.89 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	148.84 m³·mol^-1	ChemAxon
Polarizability	60.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0000000090-ec4e884f5d1e3e37a84f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0020002090-d8ff0c2813768e3cf012	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00dj-0009850000-7a1ca449a56d19c39ea8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0fk9-0009120000-a8c863a64d387cfd461a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0kmi-0496000000-bff588cc0e98918355e8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05fu-0492000000-4a9469f17183d2f9f291	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0020003090-7423fd2df7e59f0f78ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0fka-0008951000-ea0d52cf6d356a7f3590	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0fk9-0029120000-e5ff4d33e064ff47ff49	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0kmi-0395000000-775d49075e4ad66be119	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05i1-0492000000-1a8b12a2e372f5b00ca1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0000000090-262fc3f19d8442742408	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Biological Properties

Cellular Locations

Not Available

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB01362	Not Applicable	details
Urine	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB01362	Not Applicable	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01362

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iohexol

NuGOwiki Link

HMDB15449

Metagene Link

HMDB15449

METLIN ID

Not Available

PubChem Compound

3730

PDB ID

Not Available

ChEBI ID

31709

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. [PubMed:3882609 ]
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 ]

Showing metabocard for Iohexol (HMDB15449)

Structure for HMDB15449 (Iohexol)