BITOPERTIN

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Search structure


Synonyms	Bitopertin Paliflutine R-1678 RG-1678 RO-4917838 RO-4917939 RO4917838
Status
Molecule Category	UNKNOWN
UNII	Q8L6AN59YY
EPA CompTox	DTXSID80233556


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	YUUGYIUSCYNSQR-LBPRGKRZSA-N
Smiles	C[C@H](Oc1ccc(S(C)(=O)=O)cc1C(=O)N1CCN(c2ncc(C(F)(F)F)cc2F)CC1)C(F)(F)F
InChI	InChI=1S/C21H20F7N3O4S/c1-12(20(23,24)25)35-17-4-3-14(36(2,33)34)10-15(17)19(32)31-7-5-30(6-8-31)18-16(22)9-13(11-29-18)21(26,27)28/h3-4,9-12H,5-8H2,1-2H3/t12-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H20F7N3O4S
Molecular Weight	543.46
AlogP	3.94
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	79.81
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	36.0

Bioactivity

Mechanism of Action	Action	Reference
Glycine transporter 1 inhibitor	INHIBITOR	PubMed PubMed


Protein: Glycine transporter 1 Description: Sodium- and chloride-dependent glycine transporter 1 Organism : Homo sapiens P48067 ENSG00000196517

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family	-	-	-	47	67-95

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]N-Methyl-SSR504734 from human GlyT1c expressed in cell membranes incubated for 1 hr by liquid scintillation spectrometry	Homo sapiens	47.0 nM
Inhibition of GlyT1c (unknown origin) expressed in Xenopus laevis oocytes clamped at -60 mV assessed as reduction in 10 uM glycine-induced membrane currents at 300 nM pre-treated with glycine for 1 min followed by compound dosing for 3 mins by two-electrode voltage clamp assay	Homo sapiens	67.0 %
Inhibition of GlyT1c (unknown origin) expressed in Xenopus laevis oocytes clamped at -60 mV assessed as reduction in 3000 uM glycine-induced membrane currents at 300 nM pre-treated with glycine for 1 min followed by compound dosing for 3 mins by two-electrode voltage clamp assay	Homo sapiens	95.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	8.59 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	16.56 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.09 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.15 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.15 %

Cross References

Resources	Reference
ChEMBL	CHEMBL1171829
DrugBank	DB12426
FDA SRS	Q8L6AN59YY
Guide to Pharmacology	7546
PubChem	24946690
SureChEMBL	SCHEMBL562490
ZINC	ZINC000053294258

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).