Also known as: Astx660, 1799328-86-1, Astx-660, Tolinapant, Astx 660, 2lhz9zc3yo

Molecular Formula

C₃₀H₄₂FN₅O₃

Molecular Weight

539.7 g/mol

InChI Key

YCXOHEXZVKOGEV-DNRQZRRGSA-N

FDA UNII

2LHZ9ZC3YO

Tolinapant is an orally bioavailable, non-peptidomimetic antagonist of both X chromosome-linked inhibitor of apoptosis protein (XIAP) and cellular IAP 1 (cIAP1), with potential antineoplastic and pro-apoptotic activities. Upon administration, tolinapant selectively binds to and inhibits the activity of XIAP and cIAP1. This restores and promotes the induction of apoptotic signaling pathways in cancer cells, and inactivates the nuclear factor-kappa B (NF-kB)-mediated survival pathway. XIAP and cIAP1 are overexpressed by many cancer cell types and suppress apoptosis by inhibiting the activity of certain caspases; they promote both cancer cell survival and chemotherapy resistance.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-2H-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-[[(3R)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]ethanone

2.1.2 InChI

InChI=1S/C30H42FN5O3/c1-20-14-35(25(13-32-20)15-34-9-10-39-18-21(34)2)16-28(38)36-19-30(3,4)29-27(36)12-23(26(17-37)33-29)11-22-5-7-24(31)8-6-22/h5-8,12,20-21,25,32,37H,9-11,13-19H2,1-4H3/t20-,21-,25-/m1/s1

2.1.3 InChI Key

YCXOHEXZVKOGEV-DNRQZRRGSA-N

2.1.4 Canonical SMILES

CC1CN(C(CN1)CN2CCOCC2C)CC(=O)N3CC(C4=C3C=C(C(=N4)CO)CC5=CC=C(C=C5)F)(C)C

2.1.5 Isomeric SMILES

C[C@@H]1CN([C@H](CN1)CN2CCOC[C@H]2C)CC(=O)N3CC(C4=C3C=C(C(=N4)CO)CC5=CC=C(C=C5)F)(C)C

2.2 Other Identifiers

2.2.1 UNII

2LHZ9ZC3YO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Astx-660

2. Astx660

3. Ethanone, 1-(6-((4-fluorophenyl)methyl)-2,3-dihydro-5-(hydroxymethyl)-3,3-dimethyl-1h-pyrrolo(3,2-b)pyridin-1-yl)-2-((2r,5r)-5-methyl-2-(((3r)-3-methyl-4-morpholinyl)methyl)-1-piperazinyl)-

2.3.2 Depositor-Supplied Synonyms

1. Astx660

2. 1799328-86-1

3. Astx-660

4. Tolinapant

5. Astx 660

6. 2lhz9zc3yo

7. Astx 660 [who-dd]

8. Chembl4173974

9. 1799328-86-1 (free Base)

10. 1-(6-(4-fluorobenzyl)-5-(hydroxymethyl)-3,3-dimethyl-2,3-dihydro-1h-pyrrolo[3,2-b]pyridin-1-yl)-2-((2r,5r)-5-methyl-2-(((r)-3-methylmorpholino)methyl)piperazin-1-yl)ethanone

11. Ethanone, 1-(6-((4-fluorophenyl)methyl)-2,3-dihydro-5-(hydroxymethyl)-3,3-dimethyl-1h-pyrrolo(3,2-b)pyridin-1-yl)-2-((2r,5r)-5-methyl-2-(((3r)-3-methyl-4-morpholinyl)methyl)-1-piperazinyl)-

12. Tolinapant [inn]

13. Unii-2lhz9zc3yo

14. Schembl16830758

15. Tqp0801

16. Astx660; Astx 660

17. Bcp28730

18. Ex-a2904

19. Bdbm50450046

20. Nsc804861

21. S8681

22. Cs-8216

23. Nsc-804861

24. Ac-36446

25. Ba166845

26. Hy-109565

27. A16996

28. 1-[6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2r,5r)-5-methyl-2-[[(3r)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]ethanone

2.4 Create Date

2016-02-23

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₂FN₅O₃
Molecular Weight	539.7 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	539.32716838 g/mol
Monoisotopic Mass	539.32716838 g/mol
Topological Polar Surface Area	81.2 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	824
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

Tolinapant

Tolinapant

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