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Also known as: Onc206, 1638178-87-6, Ow6lm47pnk, Onc 206, 11-benzyl-7-[(2,4-difluorophenyl)methyl]-2,5,7,11-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5-dien-8-one, 4-((2,4-difluorophenyl)methyl)-2,4,6,7,8,9-hexahydro-7-(phenylmethyl)imidazo(1,2-a)pyrido(3,4-e)pyrimidin-5(1h)-one

Molecular Formula

C₂₃H₂₂F₂N₄O

Molecular Weight

408.4 g/mol

InChI Key

ITMGVSSHWMTJRR-UHFFFAOYSA-N

FDA UNII

OW6LM47PNK

DRD2 Antagonist/ClpP Agonist ONC206 is an orally bioavailable, selective bitopic dopamine receptor D2 (DRD2) antagonist and mitochondrial caseinolytic protease P (ClpP) agonist, with potential antineoplastic activity. Upon administration, DRD2 antagonist/ClpP agonist ONC206 targets, binds to and inhibits the activity of DRD2. This may inactivate Akt (protein kinase B) and extracellular signal-regulated kinase (ERK), which may result in inhibition of the phosphatidylinositol 3-kinase (PI3K)/Akt signal transduction pathway as well as the mitogen-activated protein kinase (MAPK)/ERK-mediated pathway. This may lead to the induction of tumor cell apoptosis mediated by tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL)/death receptor type 5 (DR5; TRAIL receptor 2) signaling in tumor cells. In addition, ONC206 targets and binds to ClpP and induces proteolysis. This may disrupt mitochondrial structure and function in tumor cells and lead to tumor cell death. DRD2, a G protein-coupled receptor (GPCR), is overexpressed in various malignancies. It is activated by dopamine produced by the tumor cells or present in the tumor microenvironment (TME) and plays an important role in the pro-survival and stress signaling pathways. ONC206 is able to cross the blood-brain barrier (BBB).

1 2D Structure

ONC206

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

11-benzyl-7-[(2,4-difluorophenyl)methyl]-2,5,7,11-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5-dien-8-one

2.1.2 InChI

InChI=1S/C23H22F2N4O/c24-18-7-6-17(20(25)12-18)14-29-22(30)19-15-27(13-16-4-2-1-3-5-16)10-8-21(19)28-11-9-26-23(28)29/h1-7,12H,8-11,13-15H2

2.1.3 InChI Key

ITMGVSSHWMTJRR-UHFFFAOYSA-N

2.2 Other Identifiers

2.2.1 UNII

OW6LM47PNK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Onc206

2. 11-benzyl-7-((2,4-difluorophenyl)methyl)-2,5,7,11-tetrazatricyclo(7.4.0.02,6)trideca-1(9),5-dien-8-one

2.3.2 Depositor-Supplied Synonyms

1. Onc206

2. 1638178-87-6

3. Ow6lm47pnk

4. Onc 206

5. 11-benzyl-7-[(2,4-difluorophenyl)methyl]-2,5,7,11-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5-dien-8-one

6. 4-((2,4-difluorophenyl)methyl)-2,4,6,7,8,9-hexahydro-7-(phenylmethyl)imidazo(1,2-a)pyrido(3,4-e)pyrimidin-5(1h)-one

7. 11-benzyl-7-((2,4-difluorophenyl)methyl)-2,5,7,11-tetrazatricyclo(7.4.0.02,6)trideca-1(9),5-dien-8-one

8. Refchem:168241

9. Drd2 Antagonist/clpp Agonist Onc206

10. Unii-ow6lm47pnk

11. 7-benzyl-4-(2,4-difluorobenzyl)-1,2,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[3,4-e]pyrimidin-5(4h)-one

12. Orb1307929

13. Chembl4650311

14. Onc 206 [who-dd]

15. Schembl20464679

16. Schembl29538852

17. Onc-206, Onc206 Powder

18. Onc206?

19. Glxc-23355

20. Ex-a5759

21. Nqc17887

22. Nsc783746

23. S6853

24. Akos040742338

25. Nsc-783746

26. Da-76424

27. Ms-27016

28. Hy-135147

29. Cs-0109614

30. D87153

2.4 Create Date

2018-12-15

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₂F₂N₄O
Molecular Weight	408.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	39.2
Heavy Atom Count	30
Formal Charge	0
Complexity	733
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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