2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5'-(1H-isoindole-1,3(2H)-diylidene)bis- (CED0121000)

Record Information
Version1.0
Creation Date2016-05-19 03:49:03 UTC
Update Date2026-04-17 16:57:49 UTC
SynCED IDCED0121000
Secondary Accession Numbers
  • CHEM012056
Identification
Common Name2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5'-(1H-isoindole-1,3(2H)-diylidene)bis-
ClassSmall Molecule
Description
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5'-(1H-isoindole-1,3(2H)-diylidene)bis- belongs to the isoindoles, a subclass of isoindoles and derivatives within the organic compounds. This organic compound has the chemical formula C16H9N5O6 and an average molecular weight of 367.28 g/mol. It is utilized industrially as a pigment and is used in various plastics, including Polyvinyl Chloride, Polyurethane, Polypropylene, Low-Density Polyethylene, and High-Density Polyethylene. The compound has been detected in 19 recorded sources across multiple sectors. Within aquatic systems and sediments, it is found in freshwater, seawater, surface water, and groundwater. It is also present in drinking water and water supply sources, specifically in tap water, bottled water, desalinated water, and drinking water. In the sector of wastewater, sanitation, and biosolids, it is recorded in wastewater, unspecified wastewater, wastewater treatment effluent, and mine wastewater. Additional sources include irrigation water from agriculture and land management, as well as bilge water and ballast water from marine, shipping, and aquaculture sectors. Furthermore, it has been found in appliances, HVAC, and refrigerants, specifically in water heaters and water coolers. Recorded routes of exposure for this compound include oral, inhalation, and touch.
Contaminant Type
  • PMT
Chemical Structure
SynonymsNot Available
Chemical FormulaC16H9N5O6
Average Molecular Mass367.277 g/mol
Monoisotopic Mass367.055 g/mol
CAS Registry Number36888-99-0
IUPAC Name5-[3-(4,6-dihydroxy-2-oxo-2,5-dihydropyrimidin-5-ylidene)-2,3-dihydro-1H-isoindol-1-ylidene]-4,6-dihydroxy-2,5-dihydropyrimidin-2-one
Traditional Name5-[3-(4,6-dihydroxy-2-oxopyrimidin-5-ylidene)-2H-isoindol-1-ylidene]-4,6-dihydroxypyrimidin-2-one
SMILESOC1=NC(=O)N=C(O)C1=C1NC(C2=CC=CC=C12)=C1C(O)=NC(=O)N=C1O
InChI IdentifierInChI=1S/C16H9N5O6/c22-11-7(12(23)19-15(26)18-11)9-5-3-1-2-4-6(5)10(17-9)8-13(24)20-16(27)21-14(8)25/h1-4,17H,(H2,18,19,22,23,26)(H2,20,21,24,25,27)
InChI KeyJSBMGPVJAADXIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindoles
Direct ParentIsoindoles
Alternative Parents
Substituents
  • Barbiturate
  • Isoindole
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • Benzenoid
  • 1,3-diazinane
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrole
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.082 g/LALOGPS
logP0.46ALOGPS
logP-0.66ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area176.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.43 m³·mol⁻¹ChemAxon
Polarizability33.09 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-f090548fdfd8f2b67ab9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0093000000-c89469c240c534bfe5f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-0792000000-57bb0283d9d4c698b2c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3009000000-0900e79fa25ad44472c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9017000000-00935abd470c3c9d06c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9010000000-c6f1ea7c4c293b11f878Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
6978.0 Log mg/kg [3900:12000]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
Exposure Sources
Source IDSourceSectorReference
CEDs000003Irrigation water?Irrigation water can serve as a vector for synthetic chemical contamination due to its potential exposure to agricultural inputs such as fertilizers, pesticides, and herbicides.Agriculture & land managementNot Available
CEDs000027Water Coolers?Water coolers can be a source of synthetic chemical contamination due to various materials used in their construction and operation.Appliances, HVAC & refrigerantsNot Available
CEDs000043Water heaters?Water heaters can be a source of synthetic chemical contamination primarily through the materials and coatings used in their construction.Appliances, HVAC & refrigerantsNot Available
CEDs000050Groundwater?Groundwater serves as a vital resource for drinking water and agricultural irrigation but is increasingly susceptible to contamination from synthetic chemicals.Aquatic systems & sedimentsNot Available
CEDs000051Surface water?Surface water can serve as a significant vector for the introduction of synthetic chemical contaminants into aquatic ecosystems.Aquatic systems & sedimentsNot Available
CEDs000052Seawater?Seawater can serve as a significant reservoir for synthetic chemical contamination due to various industrial activities, including shipping, oil drilling, and coastal manufacturing.Aquatic systems & sedimentsNot Available
CEDs000053Freshwater?Freshwater bodies, including rivers, lakes, and reservoirs, can serve as significant sources of synthetic chemical contamination due to various anthropogenic activities.Aquatic systems & sedimentsNot Available
CEDs000070Stormwater 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 infrastructureNot Available
CEDs000088Waterproofing sprays?Waterproofing sprays are synthetic chemical formulations designed to create a protective barrier against moisture on various surfaces, including fabrics, wood, and masonry.Building & ConstructionNot Available
CEDs000115Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.Drinking water & water supplyNot Available
CEDs000116Tap water?Tap water can be a potential source of synthetic chemical contamination due to various industrial processes and agricultural runoff.Drinking water & water supplyNot Available
CEDs000117Bottled water?Bottled water, while perceived as a safe and convenient alternative to tap water, can be a source of synthetic chemical contamination.Drinking water & water supplyNot Available
CEDs000118Desalinated water?Desalinated water, produced through processes such as reverse osmosis or distillation, is increasingly utilized to meet freshwater demands in various regions.Drinking water & water supplyNot Available
CEDs000181Ballast water?Ballast water, taken on by ships to maintain stability and balance, often contains a diverse array of microorganisms, including bacteria, viruses, and plankton.Marine, shipping & aquacultureNot Available
CEDs000182Bilge water?Bilge water is a byproduct generated from the accumulation of water in the lowest part of a ship's hull, which may include a mixture of seawater, oil, fuel residues, and various contaminants.Marine, shipping & aquacultureNot Available
CEDs000468Industrial wastewater?Industrial wastewater is a byproduct generated during various manufacturing and processing activities, which often contains a complex mixture of organic and inorganic synthetic chemicals.Wastewater, sanitation & biosolidsNot Available
CEDs000470Wastewater treatment effluent?Wastewater treatment effluent is the liquid byproduct discharged from the treatment processes designed to remove contaminants from wastewater.Wastewater, sanitation & biosolidsNot Available
CEDs000475Mine wastewater?Mine wastewater refers to the liquid waste generated during the extraction and processing of minerals.Wastewater, sanitation & biosolidsNot Available
CEDs000477Wastewater, unspecified?Wastewater refers to water that has been adversely affected in quality by anthropogenic influence, typically through domestic, industrial, or agricultural activities.Wastewater, sanitation & biosolidsNot Available
Pathways
0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Poly [ADP-ribose] polymerase 1 structureClick to view 3D structurePoly [ADP-ribose] polymerase 1P09874HumansPredicted (SEA)
Prediction Confidence Score
0.285
Applicability Domain
0.314
Statistical Significance
0.0152
Supporting Reference Compounds
146
E-value
118.564
Poly [ADP-ribose] polymerase tankyrase-2 structureClick to view 3D structurePoly [ADP-ribose] polymerase tankyrase-2Q9H2K2HumansPredicted (SEA)
Prediction Confidence Score
0.278
Applicability Domain
0.314
Statistical Significance
0.0096
Supporting Reference Compounds
90
E-value
75.1245
Poly [ADP-ribose] polymerase tankyrase-1 structureClick to view 3D structurePoly [ADP-ribose] polymerase tankyrase-1O95271HumansPredicted (SEA)
Prediction Confidence Score
0.278
Applicability Domain
0.314
Statistical Significance
0.0118
Supporting Reference Compounds
94
E-value
91.6285
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)
Prediction Confidence Score
0.27
Applicability Domain
0.314
Statistical Significance
0.1846
Supporting Reference Compounds
793
E-value
1436.86
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)
Prediction Confidence Score
0.269
Applicability Domain
0.308
Statistical Significance
0.0686
Supporting Reference Compounds
332
E-value
533.734
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)
Prediction Confidence Score
0.264
Applicability Domain
0.3
Statistical Significance
0.0115
Supporting Reference Compounds
108
E-value
89.838
NAD(P)H dehydrogenase [quinone] 1 structureClick to view 3D structureNAD(P)H dehydrogenase [quinone] 1P05982Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.262
Applicability Domain
0.262 Low confidence
Statistical Significance
0.0012
Supporting Reference Compounds
1
E-value
9.49761
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)
Prediction Confidence Score
0.255
Applicability Domain
0.308
Statistical Significance
0.1445
Supporting Reference Compounds
472
E-value
1125.08
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)
Prediction Confidence Score
0.254
Applicability Domain
0.293 Low confidence
Statistical Significance
0.1181
Supporting Reference Compounds
425
E-value
919.555
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)
Prediction Confidence Score
0.252
Applicability Domain
0.306
Statistical Significance
0.0555
Supporting Reference Compounds
182
E-value
432.141
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)
Prediction Confidence Score
0.252
Applicability Domain
0.273 Low confidence
Statistical Significance
0.3866
Supporting Reference Compounds
1157
E-value
3009.96
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)
Prediction Confidence Score
0.252
Applicability Domain
0.268 Low confidence
Statistical Significance
0.3452
Supporting Reference Compounds
967
E-value
2687.04
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)
Prediction Confidence Score
0.25
Applicability Domain
0.273 Low confidence
Statistical Significance
0.3592
Supporting Reference Compounds
996
E-value
2796.34
Click to view 3D structureTrans-cinnamate 4-monooxygenaseQ04468Helianthus tuberosusPredicted (SEA)
Prediction Confidence Score
0.25
Applicability Domain
0.25 Low confidence
Statistical Significance
0.0028
Supporting Reference Compounds
1
E-value
22.187
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)
Prediction Confidence Score
0.25
Applicability Domain
0.269 Low confidence
Statistical Significance
0.028
Supporting Reference Compounds
88
E-value
217.822
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP14920HumansPredicted (SEA)
Prediction Confidence Score
0.25
Applicability Domain
0.282 Low confidence
Statistical Significance
0.0044
Supporting Reference Compounds
32
E-value
34.0201
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)
Prediction Confidence Score
0.249
Applicability Domain
0.26 Low confidence
Statistical Significance
0.3537
Supporting Reference Compounds
906
E-value
2753.29
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)
Prediction Confidence Score
0.249
Applicability Domain
0.308
Statistical Significance
0.1441
Supporting Reference Compounds
407
E-value
1122.04
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP00371Sus scrofaPredicted (SEA)
Prediction Confidence Score
0.248
Applicability Domain
0.306
Statistical Significance
0.0012
Supporting Reference Compounds
15
E-value
9.34191
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)
Prediction Confidence Score
0.248
Applicability Domain
0.273 Low confidence
Statistical Significance
0.427
Supporting Reference Compounds
1274
E-value
3324.01
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)
Prediction Confidence Score
0.247
Applicability Domain
0.262 Low confidence
Statistical Significance
0.3378
Supporting Reference Compounds
763
E-value
2629.75
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)
Prediction Confidence Score
0.246
Applicability Domain
0.308
Statistical Significance
0.1517
Supporting Reference Compounds
372
E-value
1181.13
Click to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ63470Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.246
Applicability Domain
0.273 Low confidence
Statistical Significance
0.0239
Supporting Reference Compounds
62
E-value
186.449
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)
Prediction Confidence Score
0.245
Applicability Domain
0.273 Low confidence
Statistical Significance
0.3374
Supporting Reference Compounds
715
E-value
2626.55
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)
Prediction Confidence Score
0.245
Applicability Domain
0.269 Low confidence
Statistical Significance
0.4057
Supporting Reference Compounds
1010
E-value
3158.11
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5488898
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available