Nitisinone - Moligand™, ≥97% , 4-hydroxyphenylpyruvate dioxygenase inhibitor, CAS No.104206-65-7, 4-hydroxyphenylpyruvate dioxygenase inhibitor

CAS: 104206-65-7 Cat. No.: N137416 Molecular Weight: 329.23 EC Number: 691-056-0

GRADE & PURITY Moligand™, ≥97%

Synonyms

FT-0672739 | NITISINONE [MART.] | 2-[2-Nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione | 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione;Nitisinone | NCI60_038570 | Orfadin (TN) | RB3134 | Q3877355 | SY047291 | 2-(2-nitro-4-trifluoromet

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Application:
Nitisinone has been used:to induce liver injury,to treat Ixodes scapularis tick cells to inhibit the activity of hydroxyphenylpyruvate dioxygenase,in supplemented water to block the accumulation of toxic metabolites in human hepatocyte engrafted mice,to study its effect on bacterial pyomelanin production

Specifications

Synonyms

FT-0672739 | NITISINONE [MART.] | 2-[2-Nitro-4-(trifluoromethyl)benzoyl]-1, 3-cyclohexanedione | 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1, 3-dione;Nitisinone | NCI60_038570 | Orfadin (TN) | RB3134 | Q3877355 | SY047291 | 2-(2-nitro-4-trifluoromet

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

Biochem/physiol Actions Nitisinone is a competitive inhibitor that reversibly inhibits 4-Hydroxyphenylpyruvate oxidase (dioxygenase). Nitisinone is used in the treatment of hereditary tyrosinemia type 1, where it blocks the degradation of tyrosine into ha

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

4-hydroxyphenylpyruvate dioxygenase inhibitor

Purity

≥97%

Product Properties

• ALogP: 2.3

Names and Identifiers

• Pubchem Sid: 488187526
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187526
• Canonical Smiles: C1CC(=O)C(C(=O)C1)C(=O)C2=C(C=C(C=C2)C(F)(F)F)[N+](=O)[O-]
• IUPAC Name: 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione
• InChIKey: OUBCNLGXQFSTLU-UHFFFAOYSA-N
• INCHI: 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
• Isomeric SMILES: C1CC(=O)C(C(=O)C1)C(=O)C2=C(C=C(C=C2)C(F)(F)F)[N+](=O)[O-]
• WGK Germany: 3
• Molecular Weight: 329.23
• Reaxy-Rn: 8639943
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8639943&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones
                • Level9 Benzoylcyclohexane-1,3-diones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones - Alkyl-phenylketones
• Direct Parent: Benzoylcyclohexane-1,3-diones
• Alternative Parents: Trifluoromethylbenzenes Nitrobenzenes Nitroaromatic compounds Benzoyl derivatives Aryl alkyl ketones Beta-diketones Cyclic ketones Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organopnictogen compounds Organonitrogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aromatic homomonocyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: C-nitro compound - (trifluoromethyl)benzenes - cyclohexanones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HPD Tclin 4-hydroxyphenylpyruvate dioxygenase (1 Activities)

Discover Target: HPD

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HPD Tclin 4-hydroxyphenylpyruvate dioxygenase (117 Activities)

Discover Target: HPD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Homo sapiens (32628 Activities)

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Associated Targets(non-human)

Ttr Transthyretin (14 Activities)

Discover Target: Ttr

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Plasma (328 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO: ≥5 mg/mL
• Sensitivity: Heat sensitive
• Melt Point(°C): 138 °C
• Molecular Weight: 329.230 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 329.051 Da
• Monoisotopic Mass: 329.051 Da
• Topological Polar Surface Area: 97.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 524.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yi-Xuan Fu, Wu-Yingzheng Guo, Nan Wang, Yi-Jie Dai, Zi-Ye Zhang, Xin-Lin Sun, Wen-Chao Yang, Guang-Fu Yang.  (2022)  Diagnosis of Bacterial Plant Diseases via a Nitroreductase-Activated Fluorescent Sensor.  ANALYTICAL CHEMISTRY,      [PMID:36469707] [10.1021/acs.analchem.2c04614]

2. Jin Dong, Yi-Xuan Fu, Bai-Feng Zheng, Meng-Xi Chen, Qiong Chen, Kandegama Wishwajith, Jiangqing Dong, Hong-Yan Lin, Guang-Fu Yang.  (2025)  Repurposing 4-Hydroxyphenylpyruvate dioxygenase inhibitors as novel agents for mosquito control: A structure-based design approach.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40412679] [10.1016/j.ijbiomac.2025.144566]