Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:59 UTC |
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HMDB ID | HMDB0015449 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Iohexol |
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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. |
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Structure | 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=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) |
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Synonyms | Value | Source |
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Iohexolum | ChEBI | N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide | ChEBI | Omnipaque | Kegg | Compound 545 | MeSH, HMDB | Iohexol 350 | MeSH, HMDB | Exypaque | MeSH, HMDB | Nycodenz | MeSH, HMDB | Iohexol injection | KEGG, HMDB |
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Chemical Formula | C19H26I3N3O9 |
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Average Molecular Weight | 821.1379 |
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Monoisotopic Molecular Weight | 820.880309705 |
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IUPAC Name | N1,N3-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide |
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Traditional Name | iohexol |
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CAS Registry Number | 66108-95-0 |
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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 |
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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) |
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InChI Key | NTHXOOBQLCIOLC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Anilides |
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Direct Parent | O-haloacetanilides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 174 - 180 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.8 g/L | Not Available | LogP | -3.05 | HANSCH,C & LEO,AJ (1985) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Iohexol,1TMS,isomer #1 | CC(=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)=C1I | 4653.9 | Semi standard non polar | 33892256 | Iohexol,1TMS,isomer #1 | CC(=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)=C1I | 4077.4 | Standard non polar | 33892256 | Iohexol,1TMS,isomer #1 | CC(=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)=C1I | 6556.8 | Standard polar | 33892256 | Iohexol,1TMS,isomer #2 | CC(=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)=C1I | 4665.6 | Semi standard non polar | 33892256 | Iohexol,1TMS,isomer #2 | CC(=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)=C1I | 4092.8 | Standard non polar | 33892256 | Iohexol,1TMS,isomer #2 | CC(=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)=C1I | 6514.0 | Standard polar | 33892256 | Iohexol,1TMS,isomer #5 | CC(=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)=C1I | 4625.1 | Semi standard non polar | 33892256 | Iohexol,1TMS,isomer #5 | CC(=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)=C1I | 4089.3 | Standard non polar | 33892256 | Iohexol,1TMS,isomer #5 | CC(=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)=C1I | 6660.5 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Iohexol GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Iohexol GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0udi-0000000090-ec4e884f5d1e3e37a84f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0udi-0020002090-d8ff0c2813768e3cf012 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-00dj-0009850000-7a1ca449a56d19c39ea8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0fk9-0009120000-a8c863a64d387cfd461a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0kmi-0496000000-bff588cc0e98918355e8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-05fu-0492000000-4a9469f17183d2f9f291 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0udi-0020003090-7423fd2df7e59f0f78ee | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0fka-0008951000-ea0d52cf6d356a7f3590 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0fk9-0029120000-e5ff4d33e064ff47ff49 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0kmi-0395000000-775d49075e4ad66be119 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-05i1-0492000000-1a8b12a2e372f5b00ca1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol LC-ESI-ITFT , positive-QTOF | splash10-0udi-0000000090-262fc3f19d8442742408 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 30V, Positive-QTOF | splash10-0fka-0008951000-ea0d52cf6d356a7f3590 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 15V, Positive-QTOF | splash10-0udi-0020003090-7423fd2df7e59f0f78ee | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 15V, Positive-QTOF | splash10-0udi-0020002090-d8ff0c2813768e3cf012 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 30V, Positive-QTOF | splash10-00dj-0009850000-7a1ca449a56d19c39ea8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 35V, Positive-QTOF | splash10-0udi-0000000090-1c4236fb036bdcb8919d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 35V, Positive-QTOF | splash10-0udi-0000000090-d2b2317c9e97d635bc75 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Iohexol 40V, Positive-QTOF | splash10-0udi-0000000090-292177f12e5c86adf917 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 10V, Positive-QTOF | splash10-0fk9-3000000690-15559409f183bedfd23b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 20V, Positive-QTOF | splash10-0h2o-5000001920-b963e6f65dbbef4c7fc5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 40V, Positive-QTOF | splash10-00dm-6000019700-febd0dbaea02e66b12d9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 10V, Negative-QTOF | splash10-014i-0000000590-85bff61bbfe55d6063c2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 20V, Negative-QTOF | splash10-0w5a-3700000920-a293fa4682474e7a56a1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iohexol 40V, Negative-QTOF | splash10-0fvl-7500007900-33f05d012fa989b6149f | 2016-08-03 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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