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Compound Detail

CHEMBL375927

(-)-DIHYDROGUAIARETICACID
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COc1cc(C[C@@H](C)[C@H](C)Cc2ccc(O)c(OC)c2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL375927
Name (-)-DIHYDROGUAIARETICACID
Phase Preclinical
Structure Type MOL
InChI Key ADFOLUXMYYCTRR-ZIAGYGMSSA-N
12
Targets
17
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

330.4
MW (Da)
4.17
ALogP
4
HBA
2
HBD
58.9
PSA (Ų)
0.80
QED
0
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 C20H26O4
MW 330.42
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.57

Activity Summary

IC50 9 meas. best 6.03
Ki 6 meas. best 6.21
EC50 2 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase
CHEMBL5337
 Ki 6.21 6.21 620.0 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 6.09 6.09 810.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 6.07 6.07 850.0 1
17-beta-hydroxysteroid dehydrogenase type 2
CHEMBL2789
 IC50 6.03 6.03 940.0 1
A549
CHEMBL392
 IC50 5.13 4.9233 7490.0 3
17-beta-hydroxysteroid dehydrogenase type 1
CHEMBL3181
 IC50 5.11 5.11 7700.0 1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 5.04 5.04 9100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.66 4.66 22000.0 1
HeLa
CHEMBL399
 EC50 4.66 4.66 22000.0 1
HL-60
CHEMBL383
 EC50 4.58 4.58 26000.0 1
HeLa
CHEMBL399
 IC50 4.58 4.58 26000.0 1
ADMET
CHEMBL612558
 IC50 4.54 4.54 29000.0 1
Glucocorticoid receptor
CHEMBL2034
 IC50 4.46 4.46 35000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase Ki = 620.0 nM 6.21 Inhibition of Candida albicans recombinant Nce103 beta-carbonic anhydrase after ... 21332115
Carbonic anhydrase 2 Ki = 810.0 nM 6.09 Inhibition of Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase a... 21332115
Beta-carbonic anhydrase 1 Ki = 850.0 nM 6.07 Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydr... 21332115
17-beta-hydroxysteroid dehydrogenase type 2 IC50 = 940.0 nM 6.03 Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1... 28319389
A549 IC50 = 7490.0 nM 5.13 Cytotoxicity against human A549 cells after 24 hrs by propidium iodide assay 19138858
A549 IC50 = 7490.0 nM 5.13 Cytotoxicity against human A549 cells after 24 hrs by YO-PRO-1 assay 19138858
17-beta-hydroxysteroid dehydrogenase type 1 IC50 = 7700.0 nM 5.11 Inhibition of human 17beta-HSD1 expressed in HEK293 cell lysates incubated for 1... 28319389
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Ki = 9100.0 nM 5.04 Inhibition of Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydr... 21332115
HeLa EC50 = 22000.0 nM 4.66 Cytotoxicity against human HeLa cells assessed as reduction in cell viability af... 28754364
NON-PROTEIN TARGET IC50 = 22000.0 nM 4.66 Cytotoxicity against human HL60 cells assessed as reduction in cell viability af... 27210431
HL-60 EC50 = 26000.0 nM 4.58 Cytotoxicity against human HL60 cells assessed as reduction in cell viability af... 28754364
HeLa IC50 = 26000.0 nM 4.58 Cytotoxicity against human HeLa cells assessed as reduction in cell viability af... 27210431
ADMET IC50 = 29000.0 nM 4.54 Cytotoxicity against fall armyworm Sf9 cells assessed as reduction in cell viabi... 27210431
A549 IC50 = 31200.0 nM 4.51 Induction of early stage apoptosis in human A549 cells assessed as mitotracker d... 19138858
Glucocorticoid receptor IC50 = 35000.0 nM 4.46 Binding affinity to glucocorticoid receptor by GR binding assay 17583952

Literature References

PubMed DOI Target Context # Activities
21332115 10.1021/jm1013242 Unchecked 8
28333453 10.1021/acs.jnatprod.7b00035 SH-SY5Y 6
19962903 10.1016/j.bmc.2009.11.021 Unchecked 4
19138858 10.1016/j.bmc.2008.12.030 A549 3
27210431 10.1016/j.bmcl.2016.05.020 NON-PROTEIN TARGET 3
27210431 10.1016/j.bmcl.2016.05.020 Lolium multiflorum 2
21332115 10.1021/jm1013242 Carbonic anhydrase 2 2
21332115 10.1021/jm1013242 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) 1
21332115 10.1021/jm1013242 Beta-carbonic anhydrase 1 1
21332115 10.1021/jm1013242 Carbonic anhydrase 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 1 1
21332115 10.1021/jm1013242 Carbonic anhydrase 1 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 2 1
24387347 10.1021/np400772h Platelet 1
27210431 10.1016/j.bmcl.2016.05.020 Culex pipiens 1
27210431 10.1016/j.bmcl.2016.05.020 Alternaria alternata 1
27210431 10.1016/j.bmcl.2016.05.020 Fusarium solani 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 5A, mitochondrial 1
27210431 10.1016/j.bmcl.2016.05.020 Colletotrichum lagenaria 1
19962903 10.1016/j.bmc.2009.11.021 Carbonic anhydrase 5B, mitochondrial 1

Data from ChEMBL 36 via Core Engine