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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:37 UTC
HMDB IDHMDB0014416
Secondary Accession Numbers
  • HMDB14416
Metabolite Identification
Common NameDiatrizoate
DescriptionDiatrizoate is only found in individuals that have used or taken this drug. It is a commonly used x-ray contrast medium. As diatrizoate meglumine and as Diatrizoate sodium, it is used for gastrointestinal studies, angiography, and urography. [PubChem]Diatrizoate is an iodine-containing X-ray contrast agent. Iodated contrast agents were among the first contrast agents developed. Iodine is known to be particular electron-dense and to effectively scatter or stop X-rays. A good contrast agent requires a high density of electron-dense atoms. Therefore, the more iodine, the more "dense" the x-ray effect. Iodine based contrast media are water soluble and harmless to the body. These contrast agents are sold as clear colorless water solutions, the concentration is usually expressed as mg I/ml. Modern iodinated contrast agents can be used almost anywhere in the body. Most often they are used intravenously, but for various purposes they can also be used intraarterially, intrathecally (the spine) and intraabdominally - just about any body cavity or potential space.
Structure
Data?1582753177
Synonyms
ValueSource
2,4,6-Triiodo-3,5-diacetamidobenzoic acidChEBI
3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acidChEBI
Acide amidotrizoiqueChEBI
Acidum amidotrizoicumChEBI
Acidum diacetylaminotrijodbenzoicumChEBI
AmidotrizoateChEBI
Amidotrizoic acid (anhydrous)ChEBI
DiatrizoesaureChEBI
Diatrizoic acidChEBI
Diatrizoic acid (anhydrous)ChEBI
Methalamic acidChEBI
TriombrinChEBI
Urografin acidChEBI
Urogranoic acidChEBI
Amidotrizoic acidKegg
2,4,6-Triiodo-3,5-diacetamidobenzoateGenerator
3,5-Bis(acetylamino)-2,4,6-triiodobenzoateGenerator
Amidotrizoate (anhydrous)Generator
Diatrizoate (anhydrous)Generator
MethalamateGenerator
UrogranoateGenerator
DiatriazoateHMDB
Diatrizoate sodium saltHMDB
Diatrizoic acid sodium saltHMDB
Sodium amidotrizoateHMDB
Sodium diatrizoateHMDB
AmidotrezoateHMDB
Diatrizoate, sodium-magnesiumHMDB
UrothrastHMDB
UrotrastHMDB
HypaqueHMDB
Diatrizoate sodiumHMDB
Diatrizoate, sodiumHMDB
Hypaque 50HMDB
Sodium-magnesium diatrizoateHMDB
DiatrizoateChEBI
Chemical FormulaC11H9I3N2O4
Average Molecular Weight613.9136
Monoisotopic Molecular Weight613.769637046
IUPAC Name3,5-diacetamido-2,4,6-triiodobenzoic acid
Traditional Namediatrizoate
CAS Registry Number117-96-4
SMILES
CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I
InChI Identifier
InChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)
InChI KeyYVPYQUNUQOZFHG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHalobenzoic acids
Alternative Parents
Substituents
  • Halobenzoic acid
  • 4-halobenzoic acid
  • 2-halobenzoic acid
  • 4-halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-carboxy-2-haloaromatic compound
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Vinylogous halide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organohalogen compound
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP10(2.27) g/LALOGPS
logP10(2.89) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)2.17ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.13 m³·mol⁻¹ChemAxon
Polarizability38.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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]+191.82830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiatrizoateCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I4183.2Standard polar33892256
DiatrizoateCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I3103.5Standard non polar33892256
DiatrizoateCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I3544.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diatrizoate,1TMS,isomer #1CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(=O)O[Si](C)(C)C)=C1I3059.3Semi standard non polar33892256
Diatrizoate,1TMS,isomer #2CC(=O)NC1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I2854.4Semi standard non polar33892256
Diatrizoate,2TMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I2981.4Semi standard non polar33892256
Diatrizoate,2TMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I2773.0Standard non polar33892256
Diatrizoate,2TMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I3278.4Standard polar33892256
Diatrizoate,2TMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2769.6Semi standard non polar33892256
Diatrizoate,2TMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2859.4Standard non polar33892256
Diatrizoate,2TMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2803.6Standard polar33892256
Diatrizoate,3TMS,isomer #1CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2901.2Semi standard non polar33892256
Diatrizoate,3TMS,isomer #1CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2881.7Standard non polar33892256
Diatrizoate,3TMS,isomer #1CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C2607.9Standard polar33892256
Diatrizoate,1TBDMS,isomer #1CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1I3338.5Semi standard non polar33892256
Diatrizoate,1TBDMS,isomer #2CC(=O)NC1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I3117.8Semi standard non polar33892256
Diatrizoate,2TBDMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I3477.7Semi standard non polar33892256
Diatrizoate,2TBDMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I3184.6Standard non polar33892256
Diatrizoate,2TBDMS,isomer #1CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I3335.5Standard polar33892256
Diatrizoate,2TBDMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C3224.9Semi standard non polar33892256
Diatrizoate,2TBDMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C3240.3Standard non polar33892256
Diatrizoate,2TBDMS,isomer #2CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C2999.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-2000190000-1e1a0180629c7b9775202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-7000049000-3612e2236d7d0fb6b1f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diatrizoate GC-MS ("Diatrizoate,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-99b8784c2130ad6142602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03di-0009000000-41980f595b357f23008b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03di-0009000000-1577dcdfa6ca41fd47b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03e9-0069000000-8d549556fd92c5af86072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-001i-0291000000-fff2719e16023b6214af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-001i-0980000000-babd1700c93e5136416d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-000t-0930000000-b28e85bca3033f3587992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-052b-1920000000-d7d537885b4316f3992e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03di-0009000000-8d1e15522e91dc9d32432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03e9-0069000000-e6815d5eef85411e6e7d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-001i-0291000000-2032e83ba9286860a6dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-001i-0980000000-f7868434c5092c43628f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-000t-0930000000-285b756b15a887efa1b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-052e-0920000000-29b6aab602522eee1d692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOFsplash10-03di-0009000000-cf3196e4c8cdf6f33e072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate 45V, Positive-QTOFsplash10-001i-0291000000-8df60ae70ca6442cef172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate 35V, Positive-QTOFsplash10-03di-0009000000-41980f595b357f23008b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate 15V, Positive-QTOFsplash10-03di-0009000000-87773465a95c7c9582c92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diatrizoate 15V, Positive-QTOFsplash10-03di-0009000000-1577dcdfa6ca41fd47b92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 10V, Positive-QTOFsplash10-03di-0000029000-d1432154fa0a600981e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 20V, Positive-QTOFsplash10-03k9-0000097000-8609063f82dfe7f94b032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 40V, Positive-QTOFsplash10-0udi-1000090000-f972ccbdaf519374a5532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 10V, Negative-QTOFsplash10-03xr-0000095000-f0aa688e5108b5fe41042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 20V, Negative-QTOFsplash10-0229-0000094000-2f05e7ee617ec0d721132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diatrizoate 40V, Negative-QTOFsplash10-0udi-1000090000-986a25c2de253dd053a12016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00271 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00271 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00271
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2055
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiatrizoic_acid
METLIN IDNot Available
PubChem Compound2140
PDB IDNot Available
ChEBI ID53691
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 ReferencesNot Available