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Compound Detail

CHEMBL245067

PHLORIZIN
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O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL245067
Name PHLORIZIN
Phase Preclinical
Structure Type MOL
InChI Key IOUVKUPGCMBWBT-QNDFHXLGSA-N
9
Targets
57
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

436.4
MW (Da)
-0.20
ALogP
10
HBA
7
HBD
177.1
PSA (Ų)
0.29
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H24O10
MW 436.41
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 1.80

Activity Summary

IC50 41 meas. best 7.8
EC50 13 meas. best 7.46
Ki 3 meas. best 7.73

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium/glucose cotransporter 2
CHEMBL3884
 IC50 7.8 7.3379 16.0 14
Sodium/glucose cotransporter 2
CHEMBL3884
 Ki 7.73 7.73 18.6 1
Sodium/glucose cotransporter 2
CHEMBL3884
 EC50 7.46 7.1575 35.0 8
Sodium/glucose cotransporter 1
CHEMBL4979
 IC50 7.22 6.6546 60.7 13
Sodium/glucose cotransporter 2
CHEMBL4316
 IC50 7.02 7.02 96.0 1
Sodium/glucose cotransporter 1
CHEMBL4979
 EC50 6.92 6.71 120.0 5
Unchecked
CHEMBL612545
 IC50 6.8 5.2633 160.0 3
Sodium/glucose cotransporter 1
CHEMBL4979
 Ki 6.75 6.75 180.0 1
Sodium/glucose cotransporter 1
CHEMBL5374
 IC50 6.46 6.46 350.0 1
RAW264.7
CHEMBL612557
 IC50 4.84 4.84 14400.0 2
Solute carrier family 28 member 3
CHEMBL5707
 Ki 4.8 4.8 16000.0 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 4.38 4.38 41720.0 1
Sodium/nucleoside cotransporter 2
CHEMBL5780
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium/glucose cotransporter 2 IC50 = 16.0 nM 7.8 Inhibition of human SGLT2 expressed in CHO-K1 cells by [14C]AMG uptake assay 22652255
Sodium/glucose cotransporter 2 IC50 = 16.0 nM 7.8 Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]AMG uptake aft... 21873071
Sodium/glucose cotransporter 2 IC50 = 16.4 nM 7.79 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of sodiu... 22889351
Sodium/glucose cotransporter 2 Ki = 18.6 nM 7.73 Inhibition of human kidney SGLT2 assessed as renal glucose reabsorption 19243175
Sodium/glucose cotransporter 2 IC50 = 21.0 nM 7.68 Inhibition of SGLT2 (unknown origin) 37608596
Sodium/glucose cotransporter 2 IC50 = 27.8 nM 7.56 Inhibition of human SGLT2 expressed in CHOK1 cells assessed as inhibition of glu... 20302302
Sodium/glucose cotransporter 2 IC50 = 34.6 nM 7.46 Inhibition of SGLT2 (unknown origin) 32738984
Sodium/glucose cotransporter 2 IC50 = 34.6 nM 7.46 Inhibition of human SGLT2 31630053
Sodium/glucose cotransporter 2 EC50 = 35.0 nM 7.46 Inhibition of human SGLT2 expressed in CHO cells assessed as intracellular accum... 18707880
Sodium/glucose cotransporter 2 EC50 = 35.0 nM 7.46 Inhibition of human kidney SGLT2 assessed as renal glucose reabsorption 19243175
Sodium/glucose cotransporter 2 EC50 = 35.6 nM 7.45 Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of [14C]... 18260618
Sodium/glucose cotransporter 2 IC50 = 36.0 nM 7.44 Inhibition of SGLT2 21398124
Sodium/glucose cotransporter 2 IC50 = 38.0 nM 7.42 Inhibition of human SGLT2 expressed in COS7 cells assessed as reduction of [14C]... 23062824
Sodium/glucose cotransporter 2 IC50 = 58.6 nM 7.23 Inhibition of SGLT2 (unknown origin) expressed in HEK293 cells using 2-NBDG as s... 24556379
Sodium/glucose cotransporter 1 IC50 = 60.7 nM 7.22 Inhibition of SGLT1 (unknown origin) expressed in HEK293 cells using 2-NBDG as s... 24556379
Sodium/glucose cotransporter 2 IC50 = 67.3 nM 7.17 Inhibition of human SGLT2 expressed in HEK293 cells assessed as reduction in 2-d... 28098449
Sodium/glucose cotransporter 2 EC50 = 77.0 nM 7.11 Inhibition of human SGLT2 expressed in CHO-K1 cells assessed as inhibition of [1... 24071445
Sodium/glucose cotransporter 2 EC50 = 79.0 nM 7.1 Inhibition of human SGLT2 expressed in CHO cells assessed as reduction in [14C]A... 29216560
Sodium/glucose cotransporter 2 IC50 = 96.0 nM 7.02 Inhibition of rat SGLT2 expressed in COS7 cells assessed as reduction of [14C]-A... 23062824
Sodium/glucose cotransporter 2 IC50 = 100.0 nM 7.0 Inhibition of human SGLT2 expressed in COS1 cells assessed as [14C]methyl-alpha-... 17374486

Literature References

PubMed DOI Target Context # Activities
25913862 10.1016/j.bmc.2015.04.016 Tyrosinase 10
24679441 10.1016/j.bmcl.2014.03.014 RAW264.7 6
15787442 10.1021/np049698a NON-PROTEIN TARGET 6
18443109 10.1128/aac.00057-08 Unchecked 4
28098449 10.1021/acs.jmedchem.6b01134 Sodium/glucose cotransporter 2 3
521818 10.1021/np50005a008 NON-PROTEIN TARGET 3
22652255 10.1016/j.bmc.2012.04.053 Cytochrome P450 3A4 3
25815140 10.1021/ml500343r Sodium/nucleoside cotransporter 2 3
28098449 10.1021/acs.jmedchem.6b01134 Sodium/glucose cotransporter 1 3
23266182 10.1016/j.bmc.2012.11.034 Unchecked 3
23062824 10.1016/j.bmc.2012.09.037 ADMET 2
19243175 10.1021/jm8013019 Sodium/glucose cotransporter 2 2
23062824 10.1016/j.bmc.2012.09.037 Unchecked 2
18707880 10.1016/j.bmcl.2008.07.109 Sodium/glucose cotransporter 2 2
18707880 10.1016/j.bmcl.2008.07.109 Unchecked 2
23062824 10.1016/j.bmc.2012.09.037 Sodium/glucose cotransporter 1 2
23062824 10.1016/j.bmc.2012.09.037 Rattus norvegicus 2
23266182 10.1016/j.bmc.2012.11.034 NON-PROTEIN TARGET 2
23062824 10.1016/j.bmc.2012.09.037 Sodium/glucose cotransporter 2 2
- 10.1039/C5MD00572H Unchecked 2

Data from ChEMBL 36 via Core Engine