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tezacaftor   Click here for help

GtoPdb Ligand ID: 10199

Synonyms: example 315 [US20090131492A1] | VX-661 | VX661
Approved drug PDB Ligand
tezacaftor is an approved drug (EMA & FDA (2018))
Compound class: Synthetic organic
Comment: Tezacaftor is a small molecule cystic fibrosis transmembrane conductance regulator (CFTR) modulator that was developed by Vertex Pharmaceuticals [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 113.18
Molecular weight 520.18
XLogP 2.67
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES OCC(Cn1c2cc(F)c(cc2cc1C(CO)(C)C)NC(=O)C1(CC1)c1ccc2c(c1)OC(O2)(F)F)O
Isomeric SMILES OC[C@@H](Cn1c2cc(F)c(cc2cc1C(CO)(C)C)NC(=O)C1(CC1)c1ccc2c(c1)OC(O2)(F)F)O
InChI InChI=1S/C26H27F3N2O6/c1-24(2,13-33)22-8-14-7-18(17(27)10-19(14)31(22)11-16(34)12-32)30-23(35)25(5-6-25)15-3-4-20-21(9-15)37-26(28,29)36-20/h3-4,7-10,16,32-34H,5-6,11-13H2,1-2H3,(H,30,35)/t16-/m1/s1
InChI Key MJUVRTYWUMPBTR-MRXNPFEDSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Drévillon L, Tanguy G, Hinzpeter A, Arous N, de Becdelièvre A, Aissat A, Tarze A, Goossens M, Fanen P. (2011)
COMMD1-mediated ubiquitination regulates CFTR trafficking.
PLoS One, 6 (3): e18334. [PMID:21483833]
2. Fernández Massó JR, Oliva Argüelles B, Tejeda Y, Astrada S, Garay H, Reyes O, Delgado-Roche L, Bollati-Fogolín M, Vallespí MG. (2013)
The Antitumor Peptide CIGB-552 Increases COMMD1 and Inhibits Growth of Human Lung Cancer Cells.
J Amino Acids, 2013: 251398. [PMID:23401744]
3. Gomez Rodriguez Y, Oliva Arguelles B, Riera-Romo M, Fernandez-De-Cossio J, Garay HE, Fernandez Masso J, Guerra Vallespi M. (2022)
Synergic effect of anticancer peptide CIGB-552 and Cisplatin in lung cancer models.
Mol Biol Rep, 49 (4): 3197-3212. [PMID:35094208]
4. Ruah SSH, Grootenhuis PDJ, Van Goor F, Zhou J, Bear B, Miller MT, McCartney J, Numa MMD. (2009)
Indole derivatives as CFTR modulators.
Patent number: US20090131492A1. Assignee: ertex Pharmaceuticals Inc. Priority date: 07/04/2006. Publication date: 21/05/2009.
5. Tanguy G, Drévillon L, Arous N, Hasnain A, Hinzpeter A, Fritsch J, Goossens M, Fanen P. (2008)
CSN5 binds to misfolded CFTR and promotes its degradation.
Biochim Biophys Acta, 1783 (6): 1189-99. [PMID:18267124]