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Compound Detail

CHEMBL183937

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Cc1cc(O)c(C(=O)CCc2ccc3occc3c2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL183937
Phase Preclinical
Structure Type MOL
InChI Key GMYFQAHYWIYNES-PFKOEMKTSA-N
2
Targets
17
Activities
3
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

458.5
MW (Da)
1.44
ALogP
9
HBA
5
HBD
149.8
PSA (Ų)
0.33
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H26O9
MW 458.46
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness 1.56

Activity Summary

IC50 9 meas. best 8.36
EC50 6 meas. best 8.28
Ki 2 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium/glucose cotransporter 2
CHEMBL3884
 Ki 8.4 8.4 4.0 1
Sodium/glucose cotransporter 2
CHEMBL3884
 IC50 8.36 7.972 4.4 5
Sodium/glucose cotransporter 2
CHEMBL3884
 EC50 8.28 7.985 5.2 4
Sodium/glucose cotransporter 1
CHEMBL4979
 Ki 7.3 7.3 50.0 1
Sodium/glucose cotransporter 1
CHEMBL4979
 IC50 6.86 6.73 139.0 4
Sodium/glucose cotransporter 1
CHEMBL4979
 EC50 6.68 6.65 211.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 956.81 ng.hr.mL-1 Rattus norvegicus
AUC 153.0 ng.hr.mL-1 Rattus norvegicus
CL 53.1 mL.min-1.kg-1 Rattus norvegicus
CL 125.1 mL.min-1.kg-1 Rattus norvegicus
T1/2 0.4 hr Homo sapiens
T1/2 0.97 hr Rattus norvegicus
T1/2 1.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium/glucose cotransporter 2 Ki = 4.0 nM 8.4 In vitro inhibition of Na-dependent [14C]AMG uptake in CHO-K1 cells expressing h... 15380212
Sodium/glucose cotransporter 2 IC50 = 4.4 nM 8.36 Inhibition of SGLT2 (unknown origin) 37608596
Sodium/glucose cotransporter 2 EC50 = 5.2 nM 8.28 Inhibition of human SGLT2 expressed in xenopus oocytes assessed as inhibition of... 35924548
Sodium/glucose cotransporter 2 IC50 = 5.2 nM 8.28 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of [14C]... 20690635
Sodium/glucose cotransporter 2 EC50 = 6.6 nM 8.18 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of [14C]... 18260618
Sodium/glucose cotransporter 2 EC50 = 6.6 nM 8.18 Inhibition of human kidney SGLT2 assessed as renal glucose reabsorption 19243175
Sodium/glucose cotransporter 2 IC50 = 11.0 nM 7.96 Inhibitory activity towards human SGLT2 expressed in CHO-K1 cells 16198559
Sodium/glucose cotransporter 2 IC50 = 11.0 nM 7.96 Inhibitory activity against SGLT2 expressed in CHO-K1 cells 16380256
Sodium/glucose cotransporter 2 IC50 = 50.0 nM 7.3 Inhibition of human kidney SGLT2 assessed as renal glucose reabsorption 19243175
Sodium/glucose cotransporter 2 EC50 = 50.0 nM 7.3 Inhibition of human SGLT2 expressed in Xenopus oocyte assessed as [14C]alpha-met... 18707880
Sodium/glucose cotransporter 1 Ki = 50.0 nM 7.3 In vitro inhibition of Na-dependent [14C]AMG uptake in CHO-K1 cells expressing h... 15380212
Sodium/glucose cotransporter 1 IC50 = 139.0 nM 6.86 Inhibitory activity towards human SGLT1 expressed in CHO-K1 cells 16198559
Sodium/glucose cotransporter 1 IC50 = 139.0 nM 6.86 Inhibitory activity against SGLT1 expressed in CHO-K1 cells 16380256
Sodium/glucose cotransporter 1 EC50 = 211.0 nM 6.68 Inhibition of human SGLT1 expressed in CHO cells assessed as inhibition of [14C]... 18260618
Sodium/glucose cotransporter 1 EC50 = 240.0 nM 6.62 Inhibition of human SGLT1 expressed in xenopus oocytes assessed as inhibition of... 35924548
Sodium/glucose cotransporter 1 IC50 = 240.0 nM 6.62 Inhibition of human SGLT1 expressed in CHO cells assessed as inhibition of [14C]... 20690635
Sodium/glucose cotransporter 1 IC50 = 260.0 nM 6.58 Inhibition of SGLT1 (unknown origin) 37608596

Literature References

PubMed DOI Target Context # Activities
20690635 10.1021/jm100332n Rattus norvegicus 4
16380256 10.1016/j.bmcl.2005.12.006 Rattus norvegicus 4
15380212 10.1016/j.bmcl.2004.07.082 ADMET 2
19243175 10.1021/jm8013019 Sodium/glucose cotransporter 2 2
18260618 10.1021/jm701272q Sodium/glucose cotransporter 2 1
37608596 10.1021/acs.jmedchem.3c01138 Unchecked 1
20690635 10.1021/jm100332n Sodium/glucose cotransporter 1 1
20690635 10.1021/jm100332n Sodium/glucose cotransporter 2 1
18707880 10.1016/j.bmcl.2008.07.109 Unchecked 1
18707880 10.1016/j.bmcl.2008.07.109 Sodium/glucose cotransporter 2 1
19243175 10.1021/jm8013019 Unchecked 1
18260618 10.1021/jm701272q Unchecked 1
18260618 10.1021/jm701272q Sodium/glucose cotransporter 1 1
10639275 10.1021/jm990175n Unchecked 1
16380256 10.1016/j.bmcl.2005.12.006 Sodium/glucose cotransporter 2 1
16380256 10.1016/j.bmcl.2005.12.006 Sodium/glucose cotransporter 1 1
16198559 10.1016/j.bmcl.2005.08.067 Sodium/glucose cotransporter 2 1
16198559 10.1016/j.bmcl.2005.08.067 Sodium/glucose cotransporter 1 1
15380212 10.1016/j.bmcl.2004.07.082 Unchecked 1
15380212 10.1016/j.bmcl.2004.07.082 Sodium/glucose cotransporter 1 1

Data from ChEMBL 36 via Core Engine