apitolisib   Click here for help

GtoPdb Ligand ID: 7888

Synonyms: GDC-0980 | GDC0980 | RG-7422 | RG7422
PDB Ligand
Compound class: Synthetic organic
Comment: Apitolisib is a dual PI3K/mTOR inhibitor. Its discovery is described in [5], where it is compound 2 (GDC-0980).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 162.07
Molecular weight 498.22
XLogP -0.63
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N1CCN(CC1)Cc1sc2c(c1C)nc(nc2N1CCOCC1)c1cnc(nc1)N)C(O)C
Isomeric SMILES O=C(N1CCN(CC1)Cc1sc2c(c1C)nc(nc2N1CCOCC1)c1cnc(nc1)N)[C@@H](O)C
InChI InChI=1S/C23H30N8O3S/c1-14-17(13-29-3-5-31(6-4-29)22(33)15(2)32)35-19-18(14)27-20(16-11-25-23(24)26-12-16)28-21(19)30-7-9-34-10-8-30/h11-12,15,32H,3-10,13H2,1-2H3,(H2,24,25,26)/t15-/m0/s1
1. Cantley LC. (2002)
The phosphoinositide 3-kinase pathway.
Science, 296 (5573): 1655-7. [PMID:12040186]
2. Guertin DA, Sabatini DM. (2007)
Defining the role of mTOR in cancer.
Cancer Cell, 12 (1): 9-22. [PMID:17613433]
3. Heckerling PS, Leikin JB, Maturen A, Terzian CG, Segarra DP. (1990)
Screening hospital admissions from the emergency department for occult carbon monoxide poisoning.
Am J Emerg Med, 8 (4): 301-4. [PMID:2094235]
4. Laplante M, Sabatini DM. (2009)
mTOR signaling at a glance.
J Cell Sci, 122 (Pt 20): 3589-94. [PMID:19812304]
5. Sutherlin DP, Bao L, Berry M, Castanedo G, Chuckowree I, Dotson J, Folks A, Friedman L, Goldsmith R, Gunzner J et al.. (2011)
Discovery of a potent, selective, and orally available class I phosphatidylinositol 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) kinase inhibitor (GDC-0980) for the treatment of cancer.
J Med Chem, 54 (21): 7579-87. [PMID:21981714]
6. Vanhaesebroeck B, Guillermet-Guibert J, Graupera M, Bilanges B. (2010)
The emerging mechanisms of isoform-specific PI3K signalling.
Nat Rev Mol Cell Biol, 11 (5): 329-41. [PMID:20379207]
7. Willemsen-Seegers N, Uitdehaag JCM, Prinsen MBW, de Vetter JRF, de Man J, Sawa M, Kawase Y, Buijsman RC, Zaman GJR. (2017)
Compound Selectivity and Target Residence Time of Kinase Inhibitors Studied with Surface Plasmon Resonance.
J Mol Biol, 429 (4): 574-586. [PMID:28043854]