Nitisinone (CED0008939)

Record Information
Version1.0
Creation Date2016-05-25 18:19:48 UTC
Update Date2026-08-19 04:02:58 UTC
Accession NumberCHEM022093
Identification
Common NameNitisinone
ClassSmall Molecule
Description
Nitisinone is an organic compound with the chemical formula C14H10F3NO5 and an average molecular weight of 329.23 g/mol. Nitisinone belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. The compound is recorded as being found in or released from six different sources. These include healthcare, pharmaceuticals, and veterinary products, specifically alimentary tract and metabolism products, as well as household cleaning and consumer products such as non electric simulated smoking devices. Additionally, it is associated with electrical and electronic equipment, including amplifiers, colour television systems, television systems, and superconducting magnets and superconducting coils. The recorded route of exposure for this substance is oral. In terms of biological activity, nitisinone acts as an inhibitor of the protein target 4-hydroxyphenylpyruvate dioxygenase (HPD).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(alpha,alpha,alpha-Trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedioneChEBI
NitisinonaChEBI
NitisinonumChEBI
OrfadinChEBI
2-(a,a,a-Trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedioneGenerator
2-(Α,α,α-trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedioneGenerator
NTBC CPDHMDB
2-(2-Nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dioneHMDB
2-(2-Nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedioneHMDB
Chemical FormulaC14H10F3NO5
Average Molecular Mass329.228 g/mol
Monoisotopic Mass329.051 g/mol
CAS Registry Number104206-65-7
IUPAC Name2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione
Traditional Namenitisinone
SMILES[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O
InChI IdentifierInChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
InChI KeyOUBCNLGXQFSTLU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoylcyclohexane-1,3-diones. These are alkyl-phenylketones where the alkyl group is a cyclohexane 1,3-dione.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentBenzoylcyclohexane-1,3-diones
Alternative Parents
Substituents
  • Benzoylcyclohexane-1,3-dione
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Benzoyl
  • Nitroaromatic compound
  • Aryl alkyl ketone
  • 1,3-diketone
  • Monocyclic benzene moiety
  • 1,3-dicarbonyl compound
  • Benzenoid
  • Organic nitro compound
  • C-nitro compound
  • Cyclic ketone
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Organofluoride
  • Organic oxide
  • Organohalogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.0081 g/LALOGPS
logP2.06ALOGPS
logP3.13ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area97.03 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.35 m³·mol⁻¹ChemAxon
Polarizability26.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01ox-9453000000-6678c582428855d7d395Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-974033c16a53de383f50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-1009000000-0631b4574f9b56f2003cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9020000000-bab1729386f1cfe2969fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-c91cd9c3e89ef6ab4236Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1009000000-beddd5d5f9f60a53de90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-9111000000-48ffa1648811e3b1568cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-0069000000-d1a96c2d31f1c560e24dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0229-0193000000-7d678116b1886af26719Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01vo-9870000000-f537fa57d0461d07f35bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-587b0e6655b2caea942fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0019000000-d789457835a608d224daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-9070000000-25cbb0124c94b26c66b7Not 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
556.0Log mg/kg[310:990]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
272Alimentary tract and metabolism productsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
Pathways
1 pathway
Nitisinone Drug Metabolism Action Pathway
Nitisinone Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structure4-hydroxyphenylpyruvate dioxygenaseQ02110Sus scrofaPredicted (SEA)0.0778492
4-hydroxyphenylpyruvate dioxygenase structureClick to view 3D structure4-hydroxyphenylpyruvate dioxygenaseP32754HumansPredicted (SEA)0.0778492
Click to view 3D structure4-hydroxyphenylpyruvate dioxygenaseP32755Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureProtoporphyrinogen oxidase, mitochondrialO24164Nicotiana tabacumPredicted (SEA)0.622794
Click to view 3D structure4-hydroxyphenylpyruvate dioxygenaseO23920Daucus carotaPredicted (SEA)2.17978
Click to view 3D structureModulator of drug activity AQ8X6S1Escherichia coli O157:H7Predicted (SEA)0.389246
Click to view 3D structureEnvelope phospholipase OPG057P04021Vaccinia virus (strain Western Reserve) (VACV) (Vaccinia virus (strainWR))Predicted (SEA)22.8877
Click to view 3D structureSRSF protein kinase 1O70551Mus musculusPredicted (SEA)63.7585
Click to view 3D structurePutative nitroreductaseQ4A0P1Staphylococcus saprophyticus subsp. saprophyticus (strain ATCC 15305 / DSM20229 / NCIMB 8711 / NCTC 7292 / S-41)Predicted (SEA)5.2159
Click to view 3D structureEukaryotic translation initiation factor 2-alpha kinase 3Q9Z1Z1Rattus norvegicusPredicted (SEA)161.304
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)2332.52
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)106.576
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)2711.72
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)3362.77
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)406.529
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)4523.9
Click to view 3D structure4-hydroxyphenylpyruvate dioxygenaseP93836Arabidopsis thalianaPredicted (SEA)0.155698
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)85.712
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)4699.99
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)3500.88
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)3254.49
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)2833.71
MAP kinase-activated protein kinase 3 structureClick to view 3D structureMAP kinase-activated protein kinase 3Q16644HumansPredicted (SEA)2219.56
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)3092.09
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)2819.85
Concentrations
Not Available
External Links
DrugBank IDDB00348
HMDB IDHMDB0014492
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNitisinone
Chemspider ID103195
ChEBI ID50378
PubChem Compound ID115355
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14668946
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15297036
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17152330
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17458044
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20883679
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21377430
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21620748
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21752152
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21813063
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21968107
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21968110
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22456946
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22885033
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23146787
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23203167
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23250512
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23311542
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23430914
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23430917
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23486607
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23511227