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Compound Detail

CHEMBL166444

METRIBOLONE
🧪 Phase II
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🧪 Phase II
C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL166444
Name METRIBOLONE
Phase Phase II
Structure Type MOL
InChI Key CCCIJQPRIXGQOE-XWSJACJDSA-N

Known Names

Methyltrienolone Metribolona Metribolone NSC-92858 R 1881 R-1881
6
Targets
24
Activities
4
Assay Types
0
PK Parameters
20
Publications
6
Known Names

Molecular Properties

284.4
MW (Da)
3.72
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.74
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -bol-; -olone

Extended Properties

Molecular Formula C19H24O2
MW 284.40
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 2.29

Activity Summary

Kd 10 meas. best 9.28
IC50 8 meas. best 9.52
Ki 4 meas. best 9.4
EC50 2 meas. best 10.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL1871
 EC50 10.89 10.425 0.0 2
Androgen receptor
CHEMBL1871
 IC50 9.52 8.5775 0.3 4
Androgen receptor
CHEMBL1871
 Ki 9.4 9.4 0.4 1
Progesterone receptor
CHEMBL208
 Ki 9.31 9.31 0.5 1
Androgen receptor
CHEMBL1871
 Kd 9.28 9.071 0.5 10
Mineralocorticoid receptor
CHEMBL1994
 Ki 9.27 9.27 0.5 1
Androgen receptor
CHEMBL3072
 IC50 8.82 8.7167 1.5 3
Sex hormone-binding globulin
CHEMBL4932
 IC50 8.43 8.43 3.7 1
Glucocorticoid receptor
CHEMBL2034
 Ki 8.02 8.02 9.7 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor EC50 = 0.013 nM 10.89 Agonist activity at human androgen receptor expressed in mouse C2C12 cells cotra... 26683992
Androgen receptor EC50 = 0.11 nM 9.96 Modulation of Androgen receptor (unknown origin) 35063736
Androgen receptor IC50 = 0.302 nM 9.52 Agonist activity at GAL4 DNA-binding domain fused androgen receptor (unknown ori... 30144697
Androgen receptor Ki = 0.4 nM 9.4 Displacement of [3H]-methyltrienolone from androgen receptor (unknown origin) ex... 26683992
Progesterone receptor Ki = 0.49 nM 9.31 Displacement of [3H]-methyltrienolone from progesterone receptor (unknown origin... 26683992
Androgen receptor Kd = 0.52 nM 9.28 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 278 K 15771445
Mineralocorticoid receptor Ki = 0.54 nM 9.27 Displacement of [3H]-aldosterone from mineralocorticoid receptor (unknown origin... 26683992
Androgen receptor Kd = 0.56 nM 9.25 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 283 K 15771445
Androgen receptor Kd = 0.6 nM 9.22 Binding affinity to androgen receptor 20355713
Androgen receptor Kd = 0.61 nM 9.21 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 273 K 15771445
Androgen receptor Kd = 0.68 nM 9.17 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 288 K 15771445
Androgen receptor Kd = 0.74 nM 9.13 Dissociation constant value of the radiolabeled compound against the androgen re... 15771445
Androgen receptor Kd = 0.99 nM 9.0 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 298 K 15771445
Androgen receptor Kd = 1.21 nM 8.92 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 303 K 15771445
Androgen receptor Kd = 1.51 nM 8.82 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 308 K 15771445
Androgen receptor IC50 = 1.5 nM 8.82 Binding affinity to rat Androgen receptor in African green monkey COS-7 cells me... 35786895
Androgen receptor IC50 = 1.5 nM 8.82 Inhibition of rat AR-mediated reporter gene expression in COS7 cells 16603353
Androgen receptor Kd = 1.95 nM 8.71 Dissociation constant for [3H]R-1881 binding to human androgen receptor at 310K 15771445
Androgen receptor IC50 = 3.09 nM 8.51 Inhibitory concentration against recombinant rat androgen receptor expressed in ... 16134935
Sex hormone-binding globulin IC50 = 3.7 nM 8.43 Inhibition of rat androgen binding protein (rABP) (n=9) 2296011

Literature References

PubMed DOI Target Context # Activities
15771445 10.1021/jm040842z Androgen receptor 18
- 10.6019/CHEMBL5058564 U2OS 8
- 10.6019/CHEMBL5058564 Fibroblast 6
- 10.6019/CHEMBL5058564 HEK-293T 5
30091920 10.1021/acs.jmedchem.8b00743 Androgen receptor 4
2296011 10.1021/jm00163a021 Sex hormone-binding globulin 3
1597861 10.1021/jm00089a024 Unchecked 3
8164266 10.1021/jm00034a022 Androgen receptor 2
3001307 10.1021/jm00151a009 Glucocorticoid receptor 2
3001307 10.1021/jm00151a009 Mineralocorticoid receptor 2
3001307 10.1021/jm00151a009 Androgen receptor 2
3001307 10.1021/jm00151a009 Progesterone receptor 2
3001307 10.1021/jm00151a009 Estrogen receptor 2
8164266 10.1021/jm00034a022 Estrogen receptor 2
30925341 10.1016/j.ejmech.2019.03.041 Androgen receptor 2
24900495 10.1021/ml3000269 Androgen receptor 2
17336533 10.1016/j.bmc.2007.02.007 Androgen receptor 2
23017882 10.1016/j.bmcl.2012.09.007 Androgen receptor 2
7877147 10.1021/jm00005a009 Androgen receptor 2
26683992 10.1021/acs.jmedchem.5b01168 Androgen receptor 2

Data from ChEMBL 36 via Core Engine