MW 270.21 Da, Purity >98%. Active metabolite of leflunomide. Inhibits dihydroorotate dehydrogenase. Shows antiproliferative effects. Active in vivo.
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Key facts
- CAS number
- 163451-81-8
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 270.21 Da
- Molecular formula
- C12H9F3N2O2
- PubChem identifier
- 54684141
- Nature
- Synthetic
Target data
Alternative names
DHOdehase, Dihydroorotate dehydrogenase, Dihydroorotate dehydrogenase (quinone), Dihydroorotate dehydrogenase mitochondrial, Dihydroorotate oxidase, Human complement of yeast URA1, POADS, PYRD_HUMAN, URA1, mitochondrial
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MW 270.21 Da, Purity >98%. Active metabolite of leflunomide. Inhibits dihydroorotate dehydrogenase. Shows antiproliferative effects. Active in vivo.
Key facts
- CAS number
- 163451-81-8
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 270.21 Da
- Molecular formula
- C12H9F3N2O2
- PubChem identifier
- 54684141
- Nature
- Synthetic
- Solubility
Soluble in DMSO.
- Biochemical name
- Teriflunomide
- Biological description
Active metabolite of leflunomide. Inhibits dihydroorotate dehydrogenase. Shows antiproliferative effects. Active in vivo.
- Canonical SMILES
- CC(=C(C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F)O
- Isomeric SMILES
- C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
- InChI
- InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
- InChIKey
- UTNUDOFZCWSZMS-YFHOEESVSA-N
- IUPAC name
- (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- -20°C
- Appropriate long-term storage conditions
- -20°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Notes
This product is manufactured by BioVision, an Abcam company and was previously called 1973 A77 1726. 1973-25 is the same size as the 25 mg size of ab141480.
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
Dihydroorotate dehydrogenase (DHODH) also known as URA1 is an enzyme weighing approximately 43 kDa. It plays a critical role in the de novo pyrimidine biosynthesis pathway. DHODH is mainly expressed in the inner mitochondrial membrane where it catalyzes the conversion of dihydroorotate to orotate. This reaction involves ubiquinone as an electron acceptor making DHODH an important player in cellular respiration. Its functionality is essential for the synthesis of nucleotides particularly in rapidly proliferating cells.
- Biological function summary
Dihydroorotate dehydrogenase is involved in establishing the pyrimidine pool necessary for DNA and RNA synthesis. It is a single-component enzyme but its activity supports the function of other enzymes in the pathway such as carbamoyl-phosphate synthetase. The proper regulation of DHODH is integral to cellular proliferation and immune responses. Cells that synthesize nucleotides at high rates such as immune cells and cancer cells heavily depend on its activity.
- Pathways
Dihydroorotate dehydrogenase is an important player in the pyrimidine biosynthesis pathway and links to the mitochondrial electron transport chain. Its interaction with ubiquinone underlines its role in energy production connecting it to respiratory complexes. DHODH works alongside proteins such as orotate phosphoribosyltransferase which further transforms orotate to orotidine-5'-monophosphate in pyrimidine biosynthesis. These pathways are vital for maintaining the balance of nucleotide levels impacting processes like DNA replication.
- Associated diseases and disorders
Dihydroorotate dehydrogenase is relevant to autoimmune diseases like rheumatoid arthritis and cancers. Inhibitors such as leflunomide and brequinar target DHODH to disrupt the proliferation of rapidly dividing cells. Leflunomide which is metabolized to teriflunomide reduces immune cell turnover in rheumatoid arthritis illustrating DHODH's therapeutic importance. Similarly it is a target in cancer treatment where its inhibition can slow down tumor growth interfacing with other metabolic regulators active in malignancies.
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Chemical Structure - A771726 (Teriflunomide), Active metabolite of leflunomide. Dihydroorotate dehydrogenase inhibitor. (ab141480)
2D chemical structure image of ab141480, A771726 (Teriflunomide), Active metabolite of leflunomide. Dihydroorotate dehydrogenase inhibitor.
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