3-acetylamino-5-(2-hydroxy-ethylcarbamoyl)-2,4,6-triiodo-benzoate (CED0116973)

Record Information

Version

1.0

Creation Date

2016-06-03 11:16:39 UTC

Update Date

2026-08-18 15:57:42 UTC

Accession Number

CHEM043791

Identification

Common Name

3-acetylamino-5-(2-hydroxy-ethylcarbamoyl)-2,4,6-triiodo-benzoate

Class

Small Molecule

Description

3-acetylamino-5-(2-hydroxy-ethylcarbamoyl)-2,4,6-triiodo-benzoate belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 643.94 g/mol, 3-acetylamino-5-(2-hydroxy-ethylcarbamoyl)-2,4,6-triiodo-benzoate is a heavy molecule. Its chemical formula is C12H11I3N2O5. This compound is utilized as iodinated X-ray contrast media. It has been found in or released from 22 recorded sources across various sectors. In aquatic systems and sediments, it is present in groundwater, surface water, seawater, and freshwater. It is also detected in drinking water and water supply sources, including tap water, bottled water, and desalinated water. Within the wastewater, sanitation, and biosolids sector, it appears in industrial wastewater, wastewater treatment effluent, mine wastewater, and unspecified wastewater. Additionally, the compound is associated with appliances, HVAC, and refrigerants, specifically in water coolers and water heaters, as well as marine, shipping, and aquaculture sources such as ballast water and bilge water. Five more sectors have also been recorded. Exposure routes for 3-acetylamino-5-(2-hydroxy-ethylcarbamoyl)-2,4,6-triiodo-benzoate include inhalation, oral, and touch.

Contaminant Type

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Acetamido-2,4,6-triiodo-N-(2-hydroxyethyl)-isophthalamic acid	ChEBI
Acide ioxitalamique	ChEBI
Acido ioxitalamico	ChEBI
Acidum ioxitalamicum	ChEBI
5-Acetamido-2,4,6-triiodo-N-(2-hydroxyethyl)-isophthalamate	Generator
Ioxitalamate	Generator
Ioxitalamic acid	ChEBI
Iooxitalamate	Generator
Vasobrix	MeSH
Sodium ioxithalamate	MeSH
Telebrix	MeSH
Ioxitalamic acid, sodium salt	MeSH
Agelix	MeSH
Telebrix 38	MeSH
5-acetamido-N-(2- Hydroxyethyl)-2,4,6-triiodoisophthalamic acid	MeSH
Ioxithalamate	MeSH

Chemical Formula

C₁₂H₁₁I₃N₂O₅

Average Molecular Mass

643.942 g/mol

Monoisotopic Mass

643.780 g/mol

CAS Registry Number

28179-44-4

IUPAC Name

3-[(2-hydroxyethyl)-C-hydroxycarbonimidoyl]-5-[(1-hydroxyethylidene)amino]-2,4,6-triiodobenzoic acid

Traditional Name

ioxitalamic acid

SMILES

CC(O)=NC1=C(I)C(C(O)=NCCO)=C(I)C(C(O)=O)=C1I

InChI Identifier

InChI=1S/C12H11I3N2O5/c1-4(19)17-10-8(14)5(11(20)16-2-3-18)7(13)6(9(10)15)12(21)22/h18H,2-3H2,1H3,(H,16,20)(H,17,19)(H,21,22)

InChI Key

OLAOYPRJVHUHCF-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Halobenzoic 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
Alkanolamine
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
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organoiodine compound (CHEBI:83517 )
dicarboxylic acid monoamide (CHEBI:83517 )
acetamides (CHEBI:83517 )
benzoic acids (CHEBI:83517 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	1.64	ALOGPS
logP	3.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	1.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	122.71 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.81 m³·mol⁻¹	ChemAxon
Polarizability	41.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00o4-1000092000-4d0bfcc42ab57d505f4b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0000290000-bea113afa507d4f83832	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0560-0030892000-be529b9a08f8ec10951a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0069500000-5cf1940320c530eb1e63	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0019000000-95d4fdffc3e831a916f0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0279000000-d3d29cce5fe216a78e8c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kmj-0592000000-c952e97f08d9e00a87c7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a59-2940000000-1cba0b7e9f97e41f9238	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0560-0030971000-6f60254e136f17e3c7b3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0069600000-97414d2d7897ddd2088d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0019000000-afc026d3c384eece14d6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0279000000-a9562bb10633969544f8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0zn9-0693000000-c7be2a986262c009581b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a59-2960000000-f8600c7dcbad916b1faf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0000290000-d74c380fe3cfa9ff6047	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0000290000-d505d6277b2b58a41c37	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0560-0030892000-be529b9a08f8ec10951a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0019000000-406a3448f9a9652df1b7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0069500000-5cf1940320c530eb1e63	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0019000000-afc026d3c384eece14d6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0000290000-2f482295e710a9846469	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0069600000-97414d2d7897ddd2088d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0560-0030971000-6f60254e136f17e3c7b3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f96-1000039000-6b3627022bf3f39cd930	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0inc-5000069000-aa0ffaabbe76434e8808	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001c-4000090000-90311b76973f8d3690ca	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0007-2000097000-e33fe1f04ce368a85256	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kml-7000169000-e7f0b52fafb938dfc09c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9000030000-db0fb6341a4b881daedf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000009000-598967d027a263752d6a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-0000059000-33ed31b5a73067f64c2b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000290000-12392b8cb3dda9880e22	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000039000-448b445bef3938bc35ed	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0295-0000092000-f7fd5b57c7a23a09b39f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fw9-0200190000-0c20485f5aef3a6d2a64	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5349.0	Log mg/kg	[3000:9500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
3	Irrigation water	Agriculture & land management	Not Available
27	Water Coolers	Appliances, HVAC & refrigerants	Not Available
43	Water heaters	Appliances, HVAC & refrigerants	Not Available
50	Groundwater	Aquatic systems & sediments	Not Available
51	Surface water	Aquatic systems & sediments	Not Available
52	Seawater	Aquatic systems & sediments	Not Available
53	Freshwater	Aquatic systems & sediments	Not Available
70	Stormwater runoff	Automotive & urban infrastructure	Not Available
88	Waterproofing sprays	Building & Construction	Not Available
115	Drinking water	Drinking water & water supply	Not Available
116	Tap water	Drinking water & water supply	Not Available
117	Bottled water	Drinking water & water supply	Not Available
118	Desalinated water	Drinking water & water supply	Not Available
181	Ballast water	Marine, shipping & aquaculture	Not Available
182	Bilge water	Marine, shipping & aquaculture	Not Available
417	X-ray contrast media, iodinated	Healthcare, pharmaceuticals & veterinary products	Not Available
468	Industrial wastewater	Wastewater, sanitation & biosolids	Not Available
470	Wastewater treatment effluent	Wastewater, sanitation & biosolids	Not Available
475	Mine wastewater	Wastewater, sanitation & biosolids	Not Available
477	Wastewater, unspecified	Wastewater, sanitation & biosolids	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Ioxitalamic acid Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	5853.72
Click to view 3D structure	Thyroid hormone receptor alpha	P10827	Humans	Predicted (SEA)	2908.6
Click to view 3D structure	Thyroid hormone receptor beta	P10828	Humans	Predicted (SEA)	3911.53
Click to view 3D structure	Solute carrier organic anion transporter family member 1C1	Q9ERB5	Mus musculus	Predicted (SEA)	269.981
Click to view 3D structure	Tyrosine 3-monooxygenase	P04177	Rattus norvegicus	Predicted (SEA)	386.288
Click to view 3D structure	Neuraminidase	P03468	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	Predicted (SEA)	1943.43
Click to view 3D structure	Neuraminidase	B4URF0	Influenza A virus	Predicted (SEA)	1869.55
Click to view 3D structure	Ornithine aminotransferase, mitochondrial	P04181	Humans	Predicted (SEA)	113.738
Click to view 3D structure	Trans-cinnamate 4-monooxygenase	Q04468	Helianthus tuberosus	Predicted (SEA)	555.921
Click to view 3D structure	Retinoic acid receptor RXR-alpha	P19793	Humans	Predicted (SEA)	5554.93
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	4315.1
Click to view 3D structure	Sialidase	P10481	Clostridium perfringens	Predicted (SEA)	703.757
Click to view 3D structure	Neuraminidase	A5Z252	Influenza A virus	Predicted (SEA)	1799.72
Click to view 3D structure	Complement factor D	P32038	Rattus norvegicus	Predicted (SEA)	844.586
Click to view 3D structure	Neuraminidase	P03474	Influenza B virus (strain B/Lee/1940)	Predicted (SEA)	740.735
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	7304.51
Click to view 3D structure	Ras-related protein Rab-2A	P61019	Humans	Predicted (SEA)	619.291
Click to view 3D structure	Sialidase-3	Q9UQ49	Humans	Predicted (SEA)	695.972
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	7553.17
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	7138.31
Click to view 3D structure	Putative inactive group IIC secretory phospholipase A2	Q5R387	Humans	Predicted (SEA)	278.311
Click to view 3D structure	Asialoglycoprotein receptor 1	P07306	Humans	Predicted (SEA)	120.9
Click to view 3D structure	Transcription factor SOX-18	P43680	Mus musculus	Predicted (SEA)	1364.7
Click to view 3D structure	Transcription factor SOX-18	P35713	Humans	Predicted (SEA)	1364.7
Click to view 3D structure	Sialidase-4	Q8WWR8	Humans	Predicted (SEA)	335.997