Idoxuridine (CED0007604)

Record Information

Version

1.0

Creation Date

2016-05-22 05:04:18 UTC

Update Date

2026-08-25 08:50:42 UTC

SynCED ID

CED0007604

Secondary Accession Numbers

CHEM018217

Identification

Common Name

Idoxuridine

Class

Small Molecule

Description

Idoxuridine is an organic compound with the formula C9H11IN2O5 and an average molecular weight of 354.10 g/mol. Idoxuridine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds. This compound acts on two recorded protein targets, functioning as an inhibitor or unknown modulator of thymidine kinase (TK) and thymidine kinase, cytosolic (TK1). The substance is found in or released from six recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is associated with antiinfectives, antivirals, and chemotherapeutics. In the realm of household cleaning and consumer products, it is found in tobacco smoke filters and non-electric simulated smoking devices. Additionally, it is present in electrical and electronic equipment, specifically electrically stimulated smoking devices. Recorded routes of exposure for idoxuridine include topical and ophthalmic application.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-5-Iodo-2'-deoxyuridine	ChEBI
1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracil	ChEBI
1-beta-D-2'-Deoxyribofuranosyl-5-iodouracil	ChEBI
1beta-D-2'-Deoxyribofuranosyl-5-iodouracil	ChEBI
2'-Deoxy-5-iodouridine	ChEBI
5-Iododeoxyuridine	ChEBI
5-Iodouracil deoxyriboside	ChEBI
Idoxuridin	ChEBI
Idoxuridina	ChEBI
Idoxuridinum	ChEBI
IdU	ChEBI
Iododeoxyridine	ChEBI
Iodoxuridine	ChEBI
Joddeoxiuridin	ChEBI
Dendrid	Kegg
Herplex	Kegg
ABBR idu	Kegg
1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracil	Generator
1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracil	Generator
1-b-D-2'-Deoxyribofuranosyl-5-iodouracil	Generator
1-Β-D-2'-deoxyribofuranosyl-5-iodouracil	Generator
1b-D-2'-Deoxyribofuranosyl-5-iodouracil	Generator
1Β-D-2'-deoxyribofuranosyl-5-iodouracil	Generator
5IDU	HMDB
5IUDR	HMDB
Allergan 201	HMDB
Allergan 211	HMDB
ID2	HMDB
Idossuridina	HMDB
IDUR	HMDB
IUDR	HMDB
3H-Labeled idoxuridine	HMDB
Kerecide	HMDB
Liquifilm, herplex	HMDB
Stoxil	HMDB
5 Iodo 2' deoxyuridine	HMDB
5-Iodo-2'-deoxyuridine	HMDB
Idoxuridine, 123I-labeled	HMDB
Idoxuridine, 131I-labeled	HMDB
Idoxuridine, 3H labeled	HMDB
Herplex liquifilm	HMDB
Idoxuridine, 125I-labeled	HMDB
Idoxuridine, 3H-labeled	HMDB
Idoxuridine, radical ion (+1)	HMDB
Idoxuridine, radical ion (1-)	HMDB
Iododeoxyuridine	HMDB
Oftan-idu	HMDB
SK And F-14287	HMDB
123I-labeled idoxuridine	HMDB
125I-labeled idoxuridine	HMDB
131I-labeled idoxuridine	HMDB
5 Iododeoxyuridine	HMDB
Idoxuridine, 123I labeled	HMDB
Idoxuridine, 125I labeled	HMDB
Idoxuridine, 131I labeled	HMDB
Oftan idu	HMDB
OftanIDU	HMDB
Idoxuridine	ChEBI

Chemical Formula

C₉H₁₁IN₂O₅

Average Molecular Mass

354.099 g/mol

Monoisotopic Mass

353.971 g/mol

CAS Registry Number

54-42-2

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

idoxuridine

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O

InChI Identifier

InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChI Key

XQFRJNBWHJMXHO-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Halopyrimidine
Hydroxypyrimidine
Pyrimidone
Aryl halide
Aryl iodide
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organoiodide
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organoiodine compound (CHEBI:147675 )
pyrimidine 2'-deoxyribonucleoside (CHEBI:147675 )

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	23.4 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-0.53	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.4 m³·mol⁻¹	ChemAxon
Polarizability	26.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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	splash10-0006-9044000000-bccd33421cbd5827f9e3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0v6u-9642400000-d09550b7622d0c69b6ff	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 LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-503ffdc301f622376ef7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-e66a7d844dfee68481bf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0690000000-4c754856d776ee07cebf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ktf-5079000000-7500193a38a21df71a72	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dr-1193000000-e1259b68275318de6919	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9010000000-be831d327a49e1e8662c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0039000000-3de48ce6c73f3678a325	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01p6-4192000000-bb1a34efb9165855507d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9220000000-7322fd218a08475b9bd0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-0059000000-86cefb7305f6f5493731	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-2491000000-4255679ae8c5451c203b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-2190000000-5aa7750d1b5c22b471c8	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2800.0 Log mg/kg [1600:5000]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000070	Stormwater runoff?Stormwater runoff refers to the flow of rainwater or melted snow that does not soak into the ground and instead collects pollutants as it travels over impervious surfaces such as roads and parking lots.	Automotive & urban infrastructure	Not Available
CEDs000307	Chemotherapeutics?Chemotherapeutics are synthetic chemicals designed for the treatment of cancer and other diseases by targeting rapidly dividing cells.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000351	Antivirals?Antivirals are synthetic chemicals designed to inhibit the replication of viruses and are widely used in the treatment of viral infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000395	Antiinfectives?Anti-infectives are a class of synthetic chemicals designed to combat infections caused by bacteria, viruses, fungi, and parasites.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	Not Available
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	Not Available
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	Not Available
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	Not Available
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	Building & Construction	Not Available
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	Not Available
CEDs000692	Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000730	Contact Lens Cases?Contact lens cases are small containers designed to store contact lenses in a sterile environment, typically made from various synthetic materials including plastics such as polypropylene or polycarbonate.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	Not Available
CEDs000742	Leather Tanning?Leather tanning is a process that transforms raw animal hides into durable leather through the application of various chemicals, including chromium salts, aldehydes, and vegetable tannins.	Textiles, leather & furnishings	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

3 pathwaysPathway Source: PathBank

Idoxuridine Action Pathway

Idoxuridine Drug Metabolism

Idoxuridine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thymidine kinase, cytosolic	P04183	Humans	Predicted (SEA)	Prediction Confidence Score 0.73 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Thymidine kinase	A3RLP8	Macacine herpesvirus 1	Predicted (SEA)	Prediction Confidence Score 0.636 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 4 E-value 0.0778492
Click to view 3D structure	Thymidine kinase	P06479	Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)	Predicted (SEA)	Prediction Confidence Score 0.575 Applicability Domain 0.733 Statistical Significance 1.00e-05 Supporting Reference Compounds 10 E-value 0.0778492
Click to view 3D structure	Thymidylate synthase ThyA	P9WFR9	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.509 Applicability Domain 0.509 Statistical Significance 4.00e-05 Supporting Reference Compounds 1 E-value 0.311397
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	Prediction Confidence Score 0.501 Applicability Domain 0.527 Statistical Significance 4.00e-04 Supporting Reference Compounds 33 E-value 3.11397
Click to view 3D structure	Thymidylate kinase	P9WKE1	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.488 Applicability Domain 0.733 Statistical Significance 5.00e-05 Supporting Reference Compounds 6 E-value 0.389246
Click to view 3D structure	Thymidine kinase 2	D3ZGQ2	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.467 Applicability Domain 0.467 Statistical Significance 8.00e-05 Supporting Reference Compounds 1 E-value 0.622794
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.454 Applicability Domain 0.733 Statistical Significance 5.30e-04 Supporting Reference Compounds 24 E-value 4.12601
Click to view 3D structure	Flavin-dependent thymidylate synthase	P9WG57	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.445 Applicability Domain 0.509 Statistical Significance 4.00e-05 Supporting Reference Compounds 2 E-value 0.311397
Click to view 3D structure	Thymidine kinase, cytosolic	P27158	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.444 Applicability Domain 0.58 Statistical Significance 1.20e-04 Supporting Reference Compounds 2 E-value 0.934191
Click to view 3D structure	Thymidylate synthase	Q2TA32	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.436 Applicability Domain 0.439 Statistical Significance 8.00e-05 Supporting Reference Compounds 2 E-value 0.622794
Click to view 3D structure	Reverse transcriptase/RNaseH	Q72547	Human immunodeficiency virus 1	Predicted (SEA)	Prediction Confidence Score 0.402 Applicability Domain 0.491 Statistical Significance 0.0015 Supporting Reference Compounds 79 E-value 11.5217
Click to view 3D structure	Thymidine kinase	Q9QNF7	HHV-1	Predicted (SEA)	Prediction Confidence Score 0.402 Applicability Domain 0.694 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Thymidine kinase	P09250	HHV-3	Predicted (SEA)	Prediction Confidence Score 0.398 Applicability Domain 0.421 Statistical Significance 4.00e-05 Supporting Reference Compounds 3 E-value 0.311397
Click to view 3D structure	DNA polymerase delta catalytic subunit	P28340	Humans	Predicted (SEA)	Prediction Confidence Score 0.352 Applicability Domain 0.352 Statistical Significance 3.00e-04 Supporting Reference Compounds 1 E-value 2.33548
Click to view 3D structure	Thymidine kinase 2, mitochondrial	O00142	Humans	Predicted (SEA)	Prediction Confidence Score 0.34 Applicability Domain 0.424 Statistical Significance 1.20e-04 Supporting Reference Compounds 7 E-value 0.934191
Click to view 3D structure	Ribonuclease pancreatic	P61823	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.339 Applicability Domain 0.339 Statistical Significance 4.90e-04 Supporting Reference Compounds 1 E-value 3.81461
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Predicted (SEA)	Prediction Confidence Score 0.337 Applicability Domain 0.508 Statistical Significance 0.0014 Supporting Reference Compounds 51 E-value 10.821
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.364 Statistical Significance 0.0279 Supporting Reference Compounds 472 E-value 216.966
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.364 Statistical Significance 0.013 Supporting Reference Compounds 242 E-value 101.282
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.364 Statistical Significance 0.0193 Supporting Reference Compounds 332 E-value 150.015
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.364 Statistical Significance 0.0238 Supporting Reference Compounds 407 E-value 185.515
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.364 Statistical Significance 0.01 Supporting Reference Compounds 165 E-value 77.8492
Click to view 3D structure	Ribonuclease pancreatic	P07998	Humans	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.318 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 13.6236
Click to view 3D structure	Non-secretory ribonuclease	P10153	Humans	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.318 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 13.6236