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Compound Detail

CHEMBL486422

DAIDZIN
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O=c1c(-c2ccc(O)cc2)coc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL486422
Name DAIDZIN
Phase Preclinical
Structure Type MOL
InChI Key KYQZWONCHDNPDP-QNDFHXLGSA-N
6
Targets
10
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

416.4
MW (Da)
0.34
ALogP
9
HBA
5
HBD
149.8
PSA (Ų)
0.41
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H20O9
MW 416.38
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 1.54

Activity Summary

IC50 9 meas. best 7.4
Kd 1 meas. best 5.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldehyde dehydrogenase, mitochondrial
CHEMBL1935
 IC50 7.4 6.6533 40.0 3
Unchecked
CHEMBL612545
 IC50 7.1 5.995 80.0 2
Interleukin-2
CHEMBL5880
 Kd 5.47 5.47 3380.0 1
Retinal dehydrogenase 2
CHEMBL3112384
 IC50 5.35 5.35 4500.0 1
Aldehyde dehydrogenase X, mitochondrial
CHEMBL4881
 IC50 5.29 5.29 5100.0 1
HepG2
CHEMBL395
 IC50 4.21 4.21 61200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 120.0 nM hr ml -
Tmax 1.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldehyde dehydrogenase, mitochondrial IC50 = 40.0 nM 7.4 Inhibition of Hamster Liver mitochondrial ALDH-2 11063613
Aldehyde dehydrogenase, mitochondrial IC50 = 80.0 nM 7.1 Inhibition of hamster liver aldehyde dehydrogenase ALDH-2 11563931
Unchecked IC50 = 80.0 nM 7.1 Inhibition of hamster liver ALDH2 18613661
Interleukin-2 Kd = 3380.0 nM 5.47 Binding affinity to IL-2 (unknown origin) 24974349
Aldehyde dehydrogenase, mitochondrial IC50 = 3500.0 nM 5.46 Inhibition of full length recombinant human ALDH2 expressed in Escherichia coli ... 28219011
Retinal dehydrogenase 2 IC50 = 4500.0 nM 5.35 Inhibition of full length recombinant human ALDH1A2 expressed in Escherichia col... 28219011
Aldehyde dehydrogenase X, mitochondrial IC50 = 5100.0 nM 5.29 Inhibition of full length recombinant human ALDH1B1 expressed in Escherichia col... 28219011
Unchecked IC50 = 12900.0 nM 4.89 PUBCHEM_BIOASSAY: A biochemical assay using the ADP-Hunter methodology, purified... -
HepG2 IC50 = 61200.0 nM 4.21 Anticancer activity against human HepG2 cells assessed as cell viability after 2... 24974349

Literature References

PubMed DOI Target Context # Activities
35835380 10.1016/j.bmcl.2022.128886 i-motif DNA 12
28343876 10.1016/j.bmcl.2017.03.013 Unchecked 6
35835380 10.1016/j.bmcl.2022.128886 quadruplex DNA 6
11063613 10.1021/jm990614i Monoamine oxidase 5
11063613 10.1021/jm990614i Aldehyde dehydrogenase, mitochondrial 5
19944611 10.1016/j.bmc.2009.11.015 No relevant target 3
35835380 10.1016/j.bmcl.2022.128886 dsDNA 3
22578462 10.1016/j.bmcl.2012.04.081 Unchecked 3
11063613 10.1021/jm990614i ADMET 2
22859782 10.1124/dmd.112.045849 Plasma 2
24953601 10.1016/j.bmcl.2014.05.077 No relevant target 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
20605096 10.1016/j.bmcl.2010.06.077 3T3-L1 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
19944611 10.1016/j.bmc.2009.11.015 NON-PROTEIN TARGET 1
8882428 10.1021/np960057s Monocyte 1
24974349 10.1016/j.ejmech.2014.06.037 Interleukin-2 1
24974349 10.1016/j.ejmech.2014.06.037 HepG2 1
11563931 10.1021/jm0101390 Monoamine oxidase 1
11563931 10.1021/jm0101390 Aldehyde dehydrogenase, mitochondrial 1

Data from ChEMBL 36 via Core Engine