TOFOGLIFLOZIN

/static/temp/default.svg

Search structure


Synonyms	CSG 452 CSG-452 CSG452 R-7201 RO-4998452 RO4998452 Tofogliflozin Tofogliflozin hydrate Tofogliflozin monohydrate
Status
Molecule Category	Mixture
UNII	554245W62T
EPA CompTox	DTXSID90238097


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

Structure


InChI Key	VWVKUNOPTJGDOB-BDHVOXNPSA-N
Smiles	CCc1ccc(Cc2ccc3c(c2)[C@]2(OC3)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1
InChI	InChI=1S/C22H26O6/c1-2-13-3-5-14(6-4-13)9-15-7-8-16-12-27-22(17(16)10-15)21(26)20(25)19(24)18(11-23)28-22/h3-8,10,18-21,23-26H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H26O6
Molecular Weight	386.44
AlogP	1.0
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	4.0
Polar Surface Area	99.38
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Sodium/glucose cotransporter 2 inhibitor	INHIBITOR	PubMed


Protein: Sodium/glucose cotransporter 2 Description: Sodium/glucose cotransporter 2 Organism : Homo sapiens P31639 ENSG00000140675

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC05 family of sodium-dependent glucose transporters	-	3-4	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of sodium-dependent [14C]methyl-alpha-D-glucopyranoside uptake after 45 mins	Homo sapiens	2.9 nM
Inhibition of SGLT2 (unknown origin)	Homo sapiens	4.0 nM
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	-0.35 %
Inhibition of human SGLT2	Homo sapiens	2.9 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.15 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	3.05 %
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	0.1 %		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	0.02 %		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	0.02 %		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	0.1 %

Cross References

Resources	Reference
ChEBI	136041
ChEMBL	CHEMBL2110731
DrugBank	DB11824
DrugCentral	4892
FDA SRS	554245W62T
Guide to Pharmacology	9395
PubChem	46908928
SureChEMBL	SCHEMBL903156
ZINC	ZINC000035826342
ChEMBL	CHEMBL2105711
FDA SRS	P8DD8KX4O4
Guide to Pharmacology	9395
PubChem	46908928
SureChEMBL	SCHEMBL19328161

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).