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Compound Detail

CHEMBL207413

ACETOXOLONE
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CC(=O)O[C@H]1CC[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]2C1(C)C

Basic Information

ChEMBL ID CHEMBL207413
Name ACETOXOLONE
Phase Preclinical
Structure Type MOL
InChI Key FTQDJVZNPJRVPG-XWEVEMRCSA-N

Known Names

Acetoxolone Acetylglycyrrhetic acid Acetylglycyrrhetinic acid DGS 0110A DGS-0110A Glycyrrhetic acid acetate Glycyrrhetinic acid acetate Glycyrrhetinyl acetate NSC-35349 Uralenic acid, acetate
6
Targets
14
Activities
1
Assay Types
0
PK Parameters
20
Publications
10
Known Names
2
Indications

Molecular Properties

512.7
MW (Da)
6.98
ALogP
4
HBA
1
HBD
80.7
PSA (Ų)
0.40
QED
2
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -olone

Extended Properties

Molecular Formula C32H48O5
MW 512.73
Aromatic Rings 0
Heavy Atoms 37
NP-Likeness 3.14

Indications

Gastroesophageal Reflux Peptic Ulcer

ATC Classification

A02BX09
acetoxolone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 14 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3746
IC50 6.7 6.0325 201.0 4
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
IC50 6.1 5.465 800.0 4
17-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2789
IC50 5.42 5.42 3780.0 1
17-beta-hydroxysteroid dehydrogenase type 1
CHEMBL3181
IC50 4.73 4.73 18800.0 1
Cocaine esterase
CHEMBL3180
IC50 4.39 4.39 40510.0 1
Liver carboxylesterase 1
CHEMBL2265
IC50 4.3 4.3 49860.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 201.0 nM 6.7 Inhibition of human recombinant 11-beta-HSD2 expressed in HEK293 cells 16759088
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 750.0 nM 6.12 Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed a... 20851614
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 750.0 nM 6.12 Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as conversion... 21376605
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 800.0 nM 6.1 Inhibition of human recombinant 11-beta-HSD1 expressed in HEK293 cells 16759088
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 3450.0 nM 5.46 Inhibition of human recombinant 11-beta-HSD1 transfected in intact HEK293 cells 16759088
17-beta-hydroxysteroid dehydrogenase type 2 IC50 = 3780.0 nM 5.42 Inhibition of human recombinant 17-beta-HSD2 expressed in HEK293 cells 16759088
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 6430.0 nM 5.19 Inhibition of human recombinant 11betaHSD2 transfected in intact HEK293 cells 16759088
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 7138.0 nM 5.15 Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed a... 20851614
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 7100.0 nM 5.15 Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed a... 21376605
17-beta-hydroxysteroid dehydrogenase type 1 IC50 = 18800.0 nM 4.73 Inhibition of human recombinant 17betaHSD1 expressed in HEK293 cells 16759088
Cocaine esterase IC50 = 40510.0 nM 4.39 Inhibition of CE2 in human liver microsomes using fluorescein diacetate as subst... 26900660
Liver carboxylesterase 1 IC50 = 49860.0 nM 4.3 Inhibition of CE1 in human liver microsomes using 2-(2-Benzoyl-3-methoxyphenyl) ... 26900660

Literature References

PubMed DOI Target Context # Activities
16759088 10.1021/jm0600794 11-beta-hydroxysteroid dehydrogenase 1 3
23541646 10.1016/j.bmcl.2013.02.115 Brugia malayi 3
22520261 10.1016/j.bmcl.2012.03.081 Unchecked 3
22520261 10.1016/j.bmcl.2012.03.081 Hepatitis B virus 3
16759088 10.1021/jm0600794 11-beta-hydroxysteroid dehydrogenase type 2 2
20851614 10.1016/j.bmc.2010.08.046 11-beta-hydroxysteroid dehydrogenase 1 2
20851614 10.1016/j.bmc.2010.08.046 11-beta-hydroxysteroid dehydrogenase type 2 2
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase 1 2
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase type 2 2
26900660 10.1016/j.ejmech.2016.02.020 Unchecked 1
16759088 10.1021/jm0600794 HEK293 1
26900660 10.1016/j.ejmech.2016.02.020 Liver carboxylesterase 1 1
26900660 10.1016/j.ejmech.2016.02.020 Cocaine esterase 1
22520261 10.1016/j.bmcl.2012.03.081 ADMET 1
21376605 10.1016/j.bmc.2011.02.005 Unchecked 1
20851614 10.1016/j.bmc.2010.08.046 Unchecked 1
19914836 10.1016/j.bmc.2009.10.036 11-beta-hydroxysteroid dehydrogenase 1 1
19914836 10.1016/j.bmc.2009.10.036 11-beta-hydroxysteroid dehydrogenase type 2 1
18562200 10.1016/j.bmc.2008.05.078 Unchecked 1
16759088 10.1021/jm0600794 17-beta-hydroxysteroid dehydrogenase type 2 1

Data from ChEMBL 36 via Core Engine