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Compound Detail

CHEMBL410683

GUGGULSTERONE
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C/C=C1\C(=O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL410683
Name GUGGULSTERONE
Phase Preclinical
Structure Type MOL
InChI Key WDXRGPWQVHZTQJ-OSJVMJFVSA-N
9
Targets
26
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

312.4
MW (Da)
4.64
ALogP
2
HBA
0
HBD
34.1
PSA (Ų)
0.61
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H28O2
MW 312.45
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 2.51

Activity Summary

IC50 22 meas. best 8.62
Ki 4 meas. best 7.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
 IC50 8.62 8.62 2.4 1
Mineralocorticoid receptor
CHEMBL1994
 Ki 7.43 7.43 37.0 1
Progesterone receptor
CHEMBL208
 Ki 6.65 6.65 224.0 1
Glucocorticoid receptor
CHEMBL2034
 Ki 6.6 6.6 252.0 1
Androgen receptor
CHEMBL1871
 Ki 6.5 6.5 315.0 1
Androgen receptor
CHEMBL1871
 IC50 6.18 6.18 660.0 1
Progesterone receptor
CHEMBL208
 IC50 6.13 6.13 740.0 1
Mineralocorticoid receptor
CHEMBL1994
 IC50 5.73 5.73 1880.0 1
Unchecked
CHEMBL612545
 IC50 5.7 4.875 2000.0 2
Glucocorticoid receptor
CHEMBL2034
 IC50 5.22 5.22 6060.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.2 5.0 6309.6 6
Bile acid receptor
CHEMBL2047
 IC50 5.0 4.4275 10000.0 8
PANC-1
CHEMBL614139
 IC50 4.38 4.38 42000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nuclear receptor subfamily 1 group I member 2 IC50 = 2.4 nM 8.62 Inhibitory concentration against Pregnane X receptor 16250653
Mineralocorticoid receptor Ki = 37.0 nM 7.43 Inhibitory concentration against Mineralocorticoid receptor 16250653
Progesterone receptor Ki = 224.0 nM 6.65 Inhibitory concentration against Progesterone receptor 16250653
Glucocorticoid receptor Ki = 252.0 nM 6.6 Inhibitory concentration against Glucocorticoid receptor 16250653
Androgen receptor Ki = 315.0 nM 6.5 Inhibitory concentration against Androgen receptor 16250653
Androgen receptor IC50 = 660.0 nM 6.18 Inhibitory concentration against Androgen receptor 16250653
Progesterone receptor IC50 = 740.0 nM 6.13 Inhibitory concentration against Progesterone receptor 16250653
Mineralocorticoid receptor IC50 = 1880.0 nM 5.73 Inhibitory concentration against Mineralocorticoid receptor 16250653
Unchecked IC50 = 2000.0 nM 5.7 Antagonist activity at human FXRalpha expressed in human Hep3B cells assessed as... 28190654
Glucocorticoid receptor IC50 = 6060.0 nM 5.22 Inhibitory concentration against Glucocorticoid receptor 16250653
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Bile acid receptor IC50 = 10000.0 nM 5.0 Antagonist activity against FXR assessed as transactivation of luciferase report... 16905319
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Bile acid receptor IC50 = 12000.0 nM 4.92 Antagonist activity at FXR (unknown origin) by coactivator assay 23688559
Bile acid receptor IC50 = 12000.0 nM 4.92 Inhibition of FXR in HEK293 cells in presence of CDCA by GAL4 transactivation ac... 17292610
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
PANC-1 IC50 = 42000.0 nM 4.38 Cytotoxicity against human PANC1 cells incubated in normal DMEM medium 32057581

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
22862148 10.1021/jm3002718 Mus musculus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
18083521 10.1016/j.bmc.2007.11.062 Rattus norvegicus 3
22862148 10.1021/jm3002718 Unchecked 3
- 10.1007/s00044-010-9444-9 Rattus norvegicus 3
23688559 10.1016/j.bmc.2013.04.069 Bile acid receptor 3
17292610 10.1016/j.bmc.2007.01.046 Bile acid receptor 3
38043493 10.1016/j.ejmech.2023.115992 Bile acid receptor 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
16250653 10.1021/jm0505056 Bile acid receptor 2
19102680 10.1021/np8004453 Phospholipase A2 2
19102680 10.1021/np8004453 Bile acid receptor 2
16250653 10.1021/jm0505056 Estrogen receptor 2
32057581 10.1016/j.bmcl.2020.126964 PANC-1 2
23688559 10.1016/j.bmc.2013.04.069 Nuclear receptor subfamily 1 group I member 2 2
16250653 10.1021/jm0505056 Androgen receptor 2
16250653 10.1021/jm0505056 Progesterone receptor 2
16250653 10.1021/jm0505056 Mineralocorticoid receptor 2
22862148 10.1021/jm3002718 Bile acid receptor 2

Data from ChEMBL 36 via Core Engine