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Compound Detail

CHEMBL230006

ENOXOLONE
🧪 Phase II
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🧪 Phase II
CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12

Basic Information

ChEMBL ID CHEMBL230006
Name ENOXOLONE
Phase Phase II
Structure Type MOL
InChI Key MPDGHEJMBKOTSU-YKLVYJNSSA-N

Known Names

Enoxolona Enoxolone NSC-35347 NSC-35350
52
Targets
129
Activities
4
Assay Types
0
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

470.7
MW (Da)
6.41
ALogP
3
HBA
2
HBD
74.6
PSA (Ų)
0.46
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -olone

Extended Properties

Molecular Formula C30H46O4
MW 470.69
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 3.18

Indications

Mineralocorticoid Excess Syndrome, Apparent Skin Ulcer Depressive Disorder, Major

ATC Classification

D03AX10
enoxolone
Level 1: DERMATOLOGICALS
Level 2: PREPARATIONS FOR TREATMENT OF WOUNDS AND ULCERS

Activity Summary

IC50 113 meas. best 8.92
EC50 10 meas. best 6.05
Ki 5 meas. best 6.54
Kd 1 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3746
IC50 8.92 7.98 1.2 5
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
IC50 8.7 8.09 2.0 6
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
IC50 8.07 7.331 8.6 10
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL2391
IC50 7.05 7.05 90.0 2
Protein kinase C eta type
CHEMBL3616
Kd 6.6 6.6 250.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
Ki 6.54 6.54 290.0 1
Lactoylglutathione lyase
CHEMBL2175
Ki 6.54 6.54 290.0 1
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2908
IC50 6.44 6.44 360.0 2
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
Ki 6.38 6.38 420.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 6.28 6.28 524.8 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 6.26 6.26 549.5 1
PC-12
CHEMBL612556
EC50 6.05 6.05 890.0 1
Brugia malayi
CHEMBL613140
IC50 5.92 5.92 1200.0 1
RAW264.7
CHEMBL612557
IC50 5.89 5.89 1300.0 1
Human gammaherpesvirus 4
CHEMBL613124
EC50 5.4 5.4 4000.0 1
Aldo-keto reductase family 1 member B10
CHEMBL5983
IC50 5.31 5.31 4900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.14 4.2775 7300.0 8
Tyrosine-protein phosphatase non-receptor type 11
CHEMBL3864
IC50 5.02 5.02 9600.0 2
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
Ki 5.0 5.0 10000.0 1
Unchecked
CHEMBL612545
Ki 5.0 5.0 10000.0 1
Beta-glucuronidase
CHEMBL3217380
IC50 4.92 4.92 12150.0 1
No relevant target
CHEMBL2362975
EC50 4.8 4.8 16000.0 1
ADMET
CHEMBL612558
IC50 4.75 4.74 18000.0 2
NIH3T3
CHEMBL614822
EC50 4.73 4.73 18700.0 2
Hepatitis B virus
CHEMBL613497
IC50 4.68 4.545 20860.0 2
Liver carboxylesterase 1
CHEMBL2265
IC50 4.68 4.68 20970.0 1
Unchecked
CHEMBL612545
IC50 4.65 4.388 22300.0 5
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
IC50 4.61 4.61 24800.0 1
Human immunodeficiency virus 1
CHEMBL378
IC50 4.54 4.54 28800.0 1
MCF7
CHEMBL387
IC50 4.49 4.19 32600.0 4
A549
CHEMBL392
IC50 4.44 4.138 36150.0 5
NCI-H460
CHEMBL396
IC50 4.42 4.42 37650.0 1
HepG2
CHEMBL395
IC50 4.35 4.1567 44510.0 3
SK-OV-3
CHEMBL614925
IC50 4.34 4.34 45620.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
IC50 4.34 4.34 45800.0 1
HL-60
CHEMBL383
IC50 4.26 4.23 55280.0 2
T-24
CHEMBL614774
IC50 4.25 4.25 56780.0 1
Glycogen phosphorylase, muscle form
CHEMBL4696
IC50 4.18 4.18 66000.0 1
Tyrosine-protein phosphatase non-receptor type 6
CHEMBL3166
IC50 4.18 4.18 65400.0 1
Bel7402/5-FU
CHEMBL4483230
IC50 4.16 4.16 69770.0 1
Cocaine esterase
CHEMBL3180
IC50 4.16 4.16 69260.0 1
A2780
CHEMBL614004
IC50 4.13 4.13 74570.0 2
NCI/ADR-RES
CHEMBL613829
IC50 4.13 4.13 74490.0 1
SW-1736
CHEMBL614773
IC50 4.11 4.11 76930.0 2
HT-29
CHEMBL384
IC50 4.1 4.1 80090.0 2
A-431
CHEMBL614069
IC50 4.1 4.1 79580.0 1
HCT-8
CHEMBL613510
IC50 4.1 4.1 78850.0 2
HT-29
CHEMBL384
EC50 4.1 4.1 80090.0 1
HCT-116
CHEMBL394
IC50 4.1 4.08 78830.0 3
DLD-1
CHEMBL614285
IC50 4.09 4.09 81210.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 1.2 nM 8.92 Inhibition of human 11beta-HSD2 overexpressed in microsomal fraction of HEK293 c... 25590374
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 1.22 nM 8.91 Inhibition of human 11beta-HSD2 23747808
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 1.3 nM 8.89 Inhibition of full-length human 11beta-HSD2 expressed in HEK293 microsomal fract... 28458137
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 2.0 nM 8.7 Inhibition of mouse 11beta-HSD1 expressed in HEK293 cell microsomes assessed as ... 23747808
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 5.0 nM 8.3 Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as conversion... 18653260
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 7.4 nM 8.13 Inhibition of full-length mouse 11beta-HSD1 expressed in HEK293 microsomal fract... 28458137
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 8.6 nM 8.07 Inhibition of human 11beta HSD1 expressed in HEK293 cells assessed as assessed a... 21873057
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 8.8 nM 8.06 Inhibition of human microsomal 11beta-HSD1 overexpressed in HEK293 cells using [... 26936592
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 9.4 nM 8.03 Inhibition of mouse microsomal 11beta-HSD1 overexpressed in HEK293 cells using [... 26936592
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 10.58 nM 7.98 Inhibition of mouse 11beta-HSD1 18242087
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 11.3 nM 7.95 Inhibition of full-length human 11beta-HSD1 expressed in HEK293 microsomal fract... 28458137
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 11.78 nM 7.93 Inhibition of human 11beta-HSD1 18242087
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 13.0 nM 7.89 Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as conversion... 18653260
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 29.1 nM 7.54 Inhibition of human 11beta-HSD1 overexpressed in microsomal fraction of HEK293 c... 25590374
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 29.1 nM 7.54 Inhibition of human 11beta-HSD1 expressed in HEK293 cell microsomes assessed as ... 23747808
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 40.2 nM 7.4 Inhibition of mouse 11beta-HSD1 overexpressed in microsomal fraction of HEK293 c... 25590374
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 90.0 nM 7.05 Inhibition of 11beta-HSD1 in rat liver assessed as cortisone level 19914836
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 90.0 nM 7.05 Inhibition of rat hepatic 11beta-HSD1 21376605
Protein kinase C eta type Kd = 250.0 nM 6.6 Binding affinity to recombinant human PKCeta in after 2 hrs by microequilibrium ... 20836515
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 257.0 nM 6.59 Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed a... 20851614

Literature References

PubMed DOI Target Context # Activities
24461294 10.1016/j.bmcl.2013.12.111 NCI-H460 15
26928299 10.1021/acs.jnatprod.5b00641 Staphylococcus aureus 9
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
6677713 10.1021/np50030a003 Hepatocyte 6
23373965 10.1021/jm301652t RAW264.7 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase 1 5
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase type 2 5
21888390 10.1021/jm200285z Unchecked 5
35227979 10.1016/j.ejmech.2022.114212 Mus musculus 5
28458137 10.1016/j.ejmech.2017.04.059 11-beta-hydroxysteroid dehydrogenase 1 4
12608850 10.1021/np020372g Unchecked 4
19914836 10.1016/j.bmc.2009.10.036 11-beta-hydroxysteroid dehydrogenase type 2 4
23541646 10.1016/j.bmcl.2013.02.115 Brugia malayi 4
23747808 10.1016/j.ejmech.2013.05.010 11-beta-hydroxysteroid dehydrogenase 1 4
12608850 10.1021/np020372g Raji 4
26928299 10.1021/acs.jnatprod.5b00641 Bacillus subtilis 4
19914836 10.1016/j.bmc.2009.10.036 11-beta-hydroxysteroid dehydrogenase 1 4
17663539 10.1021/jm070295s SARS-CoV 4
22520261 10.1016/j.bmcl.2012.03.081 Unchecked 3

Data from ChEMBL 36 via Core Engine