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Compound Detail

CHEMBL41286

DIACEREIN
🧪 Phase III
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🧪 Phase III
CC(=O)Oc1cccc2c1C(=O)c1c(OC(C)=O)cc(C(=O)O)cc1C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL41286
Name DIACEREIN
Phase Phase III
Structure Type MOL
InChI Key TYNLGDBUJLVSMA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

AC-201 Ac-203 Artrodar Diacerein Diacereina Diacereine Diacerhein Diacetylrhein Diora Fisiodar M-01AX21 M01AX21 +5 more
9
Targets
13
Activities
2
Assay Types
0
PK Parameters
20
Publications
17
Known Names
14
Indications
1
Mechanisms

Molecular Properties

368.3
MW (Da)
2.01
ALogP
7
HBA
1
HBD
124.0
PSA (Ų)
0.55
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2018

Extended Properties

Molecular Formula C19H12O8
MW 368.30
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Rheumatic Diseases Osteoarthritis Osteoarthritis, Hip Osteoarthritis, Knee Arthritis, Rheumatoid Diabetes Mellitus, Type 2 Epidermolysis Bullosa Epidermolysis Bullosa Simplex Gout Pemphigoid, Bullous Severe Acute Respiratory Syndrome Thrombocytopenia Epidermolysis Bullosa Dystrophica Epidermolysis Bullosa, Junctional

ATC Classification

M01AX21
diacerein
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Activity Summary

IC50 11 meas. best 6.16
EC50 2 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL4349
 IC50 6.16 6.16 700.0 3
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
 IC50 5.82 5.82 1500.0 1
Transthyretin
CHEMBL3194
 IC50 5.27 5.27 5400.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.19 5.19 6400.0 1
Female germline-specific tumor suppressor gld-1
CHEMBL1293302
 IC50 5.14 5.14 7308.0 1
Caspase-3
CHEMBL2334
 EC50 5.1 5.1 7894.0 1
Heat shock protein HSP90
CHEMBL2095165
 IC50 5.04 5.04 9234.0 1
Caspase-7
CHEMBL3468
 EC50 4.83 4.83 14802.0 1
RAW264.7
CHEMBL612557
 IC50 4.18 4.18 65410.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
N-acylethanolamine-hydrolyzing acid amidase IC50 = 700.0 nM 6.16 Time dependent inhibition of recombinant human NAAA expressed in HEK293 cells by... 27766867
N-acylethanolamine-hydrolyzing acid amidase IC50 = 700.0 nM 6.16 Time dependent inhibition of recombinant human NAAA expressed in HEK293 cell mem... 27766867
N-acylethanolamine-hydrolyzing acid amidase IC50 = 700.0 nM 6.16 Inhibition of NAAA (unknown origin) 32191459
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 1500.0 nM 5.82 Inhibition of FTO (unknown origin) expressed in Escherichia coli BL21(DE3) using... 38805939
Transthyretin IC50 = 5400.0 nM 5.27 Inhibition of acid-mediated aggregation of TTR V30M mutant (unknown origin) expr... 34225167
ATP-binding cassette sub-family C member 4 IC50 = 6400.0 nM 5.19 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Female germline-specific tumor suppressor gld-1 IC50 = 7308.0 nM 5.14 PUBCHEM_BIOASSAY: Fluorescence polarization-based biochemical high throughput do... -
Caspase-3 EC50 = 7894.0 nM 5.1 PUBCHEM_BIOASSAY: Absorbance-based biochemical high throughput dose response ass... -
Heat shock protein HSP90 IC50 = 9234.0 nM 5.04 PUBCHEM_BIOASSAY: Tumor Hsp90 Inhibitors Dose Response Confirmation. (Class of a... -
Caspase-7 EC50 = 14802.0 nM 4.83 PUBCHEM_BIOASSAY: Counterscreen for procaspase-3 activators: absorbance-based bi... -
RAW264.7 IC50 = 65410.0 nM 4.18 Antiinflammatory activity against LPS-induced mouse RAW264.7 cells assessed as r... 34491054

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
23218603 10.1016/j.bmcl.2012.11.016 Rattus norvegicus 5
34491054 10.1021/acs.jmedchem.1c01019 RAW264.7 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
27766867 10.1021/acs.jmedchem.6b00538 N-acylethanolamine-hydrolyzing acid amidase 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
26471089 10.1016/j.bmcl.2015.10.004 Mus musculus 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
38805939 10.1016/j.ejmech.2024.116526 Alpha-ketoglutarate-dependent dioxygenase FTO 1
22901311 10.1016/j.ejmech.2012.07.053 Hydroxyapatite 1
1578486 10.1021/jm00087a014 Chymotrypsinogen A 1

Data from ChEMBL 36 via Core Engine