Tegafur (CED0003658)

Record Information
Version1.0
Creation Date2016-05-22 03:31:03 UTC
Update Date2026-08-25 05:18:23 UTC
Accession NumberCHEM016419
Identification
Common NameTegafur
ClassSmall Molecule
Description
Tegafur is an organic compound with the chemical formula C8H9FN2O3 and an average molecular weight of 200.17 g/mol. Tegafur belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. In terms of its biological activity, the compound is a recorded inhibitor of the protein target thymidylate synthase (TYMS). The compound is utilized within healthcare, pharmaceuticals, and veterinary products as an antineoplastic agent, with oral exposure being the recorded route. Tegafur is found in or released from 31 recorded sources across several categories. Within electrical and electronic equipment, it is associated with antennas, amplifiers, communication cables or conductors, adjustable resistors, and conductors or conductive bodies characterised by the conductive materials, among 12 others. In the category of household cleaning and consumer products, it is found in soap detergents, bleaching agents, perfumes within detergents and soaps, pipe accessories, and tobacco pipes, as well as one additional source. Regarding food, food processing, and cookware, the compound is linked to food preservation, the processing of meats, fermentation processes for beer, and the preparation of wine or sparkling wine. Additionally, it is found in building and construction materials, specifically in tents or canopies, fencing, and ceilings.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
AtillonKegg
1-(2-Tetrahydrofuryl)-5-fluorouracilMeSH
UftoralMeSH
FluorofurMeSH
N1-(2'-Tetrahydrofuryl)-5-fluorouracilMeSH
FutrafulMeSH
Sunfural SMeSH
1-(Tetrahydro-2-furanyl)-5-fluorouracilMeSH
UtefosMeSH
5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedioneMeSH
FtorafurMeSH
FlorafurMeSH
Chemical FormulaC8H9FN2O3
Average Molecular Mass200.169 g/mol
Monoisotopic Mass200.060 g/mol
CAS Registry Number37076-68-9
IUPAC Name5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nametegafur
SMILESFC1=CN(C2CCCO2)C(=O)NC1=O
InChI IdentifierInChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)
InChI KeyWFWLQNSHRPWKFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHalopyrimidines
Alternative Parents
Substituents
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Urea
  • Lactam
  • Azacycle
  • Oxacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
logP-0.09ALOGPS
logP0.024ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.08ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.64 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.5 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00di-9010000000-09f17e43065fd7cafc97Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0089-6900000000-0edac06a6aa07cfd4b9fNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-2190000000-6638249408dce3b6c1eeNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-014i-0090000000-dc47df1bb362c454d07dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004l-8900000000-e49614f77c1ff16cc175Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-023r-6900000000-188214f26a1d69ed533aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-47ca8a935d89153a5208Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2900000000-dd4508f1cfd9f5e41985Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9300000000-cf6a12090561a84535cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfv-3900000000-540b2f444a8582b4b2b7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003s-3900000000-719cd08b446e321daa4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-0b2c9c62c17aafd3f041Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-9100000000-a6c03573064f47986545Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fl3-9310000000-3a526507aebf2916c0adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9400000000-8d25616295ea8c4d4076Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-3c6d5eb6120100ac538dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-9600000000-dcbdad1ff740f61bef21Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-076a20100044fff1134aNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
907.0Log mg/kg[510:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureThymidylate synthase ThyAP9WFR9Mycobacterium tuberculosisPredicted (SEA)0.622794
Click to view 3D structureFlavin-dependent thymidylate synthaseP9WG57Mycobacterium tuberculosisPredicted (SEA)1.16774
Thymidine kinase, cytosolic structureClick to view 3D structureThymidine kinase, cytosolicP04183HumansPredicted (SEA)2.41333
Click to view 3D structureThymidylate synthaseP07607Mus musculusPredicted (SEA)10.7432
Thymidylate kinase structureClick to view 3D structureThymidylate kinaseP9WKE1Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)3.19182
Click to view 3D structureThymidine kinaseP06479Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)Predicted (SEA)2.72472
Click to view 3D structureThymidine kinase 2D3ZGQ2Rattus norvegicusPredicted (SEA)4.12601
Click to view 3D structureThymidine kinaseA3RLP8Macacine herpesvirus 1Predicted (SEA)1.71268
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP00469Lactobacillus caseiPredicted (SEA)20.63
Click to view 3D structureThymidine kinase, cytosolicP27158Rattus norvegicusPredicted (SEA)7.16213
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)58.5426
Click to view 3D structureThymidine phosphorylaseQ5FVR2Rattus norvegicusPredicted (SEA)2.49118
DNA polymerase delta catalytic subunit structureClick to view 3D structureDNA polymerase delta catalytic subunitP28340HumansPredicted (SEA)7.31783
5'(3')-deoxyribonucleotidase, mitochondrial structureClick to view 3D structure5'(3')-deoxyribonucleotidase, mitochondrialQ9NPB1HumansPredicted (SEA)1.55698
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)1478.98
Click to view 3D structureThymidylate synthaseQ2TA32Bos taurusPredicted (SEA)8.48557
Click to view 3D structureThymidine kinaseQ9QNF7HHV-1Predicted (SEA)8.09632
Click to view 3D structureThymidine kinase 2, mitochondrialO00142HumansPredicted (SEA)5.44945
Click to view 3D structureAcid ceramidaseQ6P7S1Rattus norvegicusPredicted (SEA)44.3741
Complement decay-accelerating factor structureClick to view 3D structureComplement decay-accelerating factorP08174HumansPredicted (SEA)39.0025
Click to view 3D structureDeoxynucleoside kinaseQ9XZT6Drosophila melanogasterPredicted (SEA)7.62922
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)3381.15
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)2977.34
Click to view 3D structureThymidine kinaseP09250HHV-3Predicted (SEA)21.7978
Click to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)136.781
Concentrations
Not Available
External Links
DrugBank IDDB09256
HMDB IDHMDB0246215
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTegafur
Chemspider ID5193
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC12673
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References