Edoxudine (CED0025340)

Record Information

Version

1.0

Creation Date

2016-05-22 05:24:14 UTC

Update Date

2026-05-14 19:33:15 UTC

Accession Number

CHEM018623

Identification

Common Name

Edoxudine

Class

Small Molecule

Description

Edoxudine is an organic compound with the chemical formula C11H16N2O5 and an average molecular weight of 256.26 g/mol. Edoxudine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds. This compound is associated with four recorded sources, including healthcare, pharmaceuticals and veterinary products where it is used as a chemotherapeutic agent. It is also found in television systems and video games categorized under electrical and electronic equipment, as well as non-electric simulated smoking devices categorized under household cleaning and consumer products. The recorded route of exposure for this substance is topical. In terms of biological activity, edoxudine interacts with two recorded protein targets, acting as an inhibitor of DNA polymerase (DNApol) and thymidine kinase, cytosolic (TK1).

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Edoxudin, (alpha)-isomer	MeSH
Edoxudin, 4-(14)C-labeled	MeSH
Edoxudin, 2-(14)C-labeled, (alpha)-isomer	MeSH
5-Ethyldeoxyuridine	MeSH
5-Ethyl-2'-deoxyuridine	MeSH
Edoxudin	MeSH
5-Ethyl-1-(2'-deoxyribofuranosyl)uracil	MeSH
2'-Deoxy-5-ethyluridine	MeSH
Edoxudin, 4-(14)C-labeled, (alpha)-isomer	MeSH
Edoxudin, 2-(14)C-labeled	MeSH
1-(2'-Deoxy-beta-D-ribofuranosyl)-5-ethyluracil	MeSH
ORF-15817RWJ-15817Eudr	ChEMBL

Chemical Formula

C₁₁H₁₆N₂O₅

Average Molecular Mass

256.258 g/mol

Monoisotopic Mass

256.106 g/mol

CAS Registry Number

15176-29-1

IUPAC Name

5-ethyl-4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

Traditional Name

β-5-ethyl-2'-deoxyuridine

SMILES

[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(CC)C(O)=NC1=O

InChI Identifier

InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1

InChI Key

XACKNLSZYYIACO-DJLDLDEBSA-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
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Vinylogous amide
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	10.6 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.31	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.33 m³·mol⁻¹	ChemAxon
Polarizability	24.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0900000000-248e77dacd89a6e85a85	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-3900000000-8751f22174ef495d9023	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-3900000000-514c9078b963a3e4acce	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0c00-1690000000-71cf6b2053aeabdd95ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-015i-3920000000-181e9eeeb6df4af91cbd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9300000000-3b2fb311c66730d12a74	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
3218.0	Log mg/kg	[1800:5700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
307	Chemotherapeutics	Healthcare, pharmaceuticals & veterinary products	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Edoxudine Action Pathway

Edoxudine Drug Metabolism

Edoxudine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thymidine kinase, cytosolic	P04183	Humans	Predicted (SEA)	0.856341
Click to view 3D structure	Thymidine kinase	P06479	Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)	Predicted (SEA)	0.467095
Click to view 3D structure	Thymidine kinase	A3RLP8	Macacine herpesvirus 1	Predicted (SEA)	0.467095
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	9.9647
Click to view 3D structure	Reverse transcriptase/RNaseH	Q72547	Human immunodeficiency virus 1	Predicted (SEA)	20.7857
Click to view 3D structure	Thymidylate synthase	Q2TA32	Bos taurus	Predicted (SEA)	2.72472
Click to view 3D structure	Thymidylate kinase	P9WKE1	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	1.79053
Click to view 3D structure	Thymidylate synthase ThyA	P9WFR9	Mycobacterium tuberculosis	Predicted (SEA)	1.32344
Click to view 3D structure	Thymidine kinase	P09250	HHV-3	Predicted (SEA)	0.700643
Click to view 3D structure	Thymidine kinase 2	D3ZGQ2	Rattus norvegicus	Predicted (SEA)	2.56902
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	9.49761
Click to view 3D structure	Thymidine kinase	P0C0E6	HHV-3	Predicted (SEA)	0.311397
Click to view 3D structure	Flavin-dependent thymidylate synthase	P9WG57	Mycobacterium tuberculosis	Predicted (SEA)	1.16774
Click to view 3D structure	Thymidine kinase, cytosolic	P27158	Rattus norvegicus	Predicted (SEA)	5.13805
Click to view 3D structure	Thymidine kinase	Q9QNF7	HHV-1	Predicted (SEA)	1.24559
Click to view 3D structure	DNA polymerase beta	P06746	Humans	Predicted (SEA)	5.2159
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	113.504
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	228.643
Click to view 3D structure	Ribonuclease pancreatic	P07998	Humans	Predicted (SEA)	27.4029
Click to view 3D structure	Non-secretory ribonuclease	P10153	Humans	Predicted (SEA)	27.4029
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	364.101
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	540.118
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	652.376
Click to view 3D structure	Cytidine deaminase	P32320	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	811.5