Structure

InChI Key MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Smiles C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O
InChI
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H28O2
Molecular Weight 288.43
AlogP 3.88
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Androgen Receptor agonist AGONIST Wikipedia FDA
Protein: Androgen Receptor

Description: Androgen receptor

Organism : Homo sapiens

P10275 ENSG00000169083
Assay Description Organism Bioactivity Reference
In vitro antagonist activity against rat prostatic androgen receptor (AR) None 3.2 nM
Binding affinity against rat prostate cytosolic Androgen receptor using [3H]mibolerone as radioligand None 4.9 nM
Inhibitory constant against rat prostate cytosol androgen receptor using [3H]mibolerone Rattus norvegicus 1.4 nM
Binding affinity to human CBG receptor (corticosteroid-binding globulins) None 190.55 nM
Inhibition of human placental aromatase Cytochrome P450 19A1 Homo sapiens 600.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 21.7 %
Inhibition of rat prostate cytosolic androgen receptor Rattus norvegicus 4.9 nM
Inhibition of [3H]mibolerone binding to cytosolic androgen receptor of rat ventral prostate Rattus norvegicus 1.413 nM
Inhibition of human androgen receptor expressed in Escherichia coli Homo sapiens 3.9 nM
Inhibitory activity against AR Homo sapiens 2.7 nM
Displacement of [3H]DHT from human SHBG Homo sapiens 14.0 nM
Binding affinity to androgen receptor None 2.7 nM
Binding affinity at AR None 2.7 nM
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 0.631 nM
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM Miconazole Homo sapiens 41.1 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM Miconazole Homo sapiens 10.5 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM Miconazole Homo sapiens 4.38 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM deoxypodophyllotoxin Homo sapiens 61.0 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM deoxypodophyllotoxin Homo sapiens 10.4 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM deoxypodophyllotoxin Homo sapiens 4.85 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM epipodophyllotoxin Homo sapiens 69.4 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM epipodophyllotoxin Homo sapiens 7.96 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM epipodophyllotoxin Homo sapiens 11.46 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM podophyllotoxin Homo sapiens 44.1 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM podophyllotoxin Homo sapiens 7.82 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM podophyllotoxin Homo sapiens 7.04 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM demethylene-deoxy-podophyllotoxin Homo sapiens 103.0 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM demethylene-deoxy-podophyllotoxin Homo sapiens 69.6 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM demethylene-deoxy-podophyllotoxin Homo sapiens 69.7 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 1 uM demethylenepodophyllotoxin Homo sapiens 95.0 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 10 uM demethylenepodophyllotoxin Homo sapiens 98.7 %
Activity of human recombinant CYP3A4 assessed as conversion of testosterone to 6-beta-hydroxytestesterone at 25 uM after 60 mins in presence of 25 uM demethylenepodophyllotoxin Homo sapiens 97.1 %
Agonist activity at androgen receptor in mouse NIH3T3 cells transiently transfected with beta-galactosidase reporter gene assessed as cellular transformation by R-SAT assay Mus musculus 1.995 nM
Agonist activity at androgen receptor in human MDA-KB2 cells transfected with MMTV linked luciferase assessed as transcriptional activation by luciferase reporter gene assay Homo sapiens 3.162 nM
Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 3 uM after 7 hrs Homo sapiens 7.5 %
Binding affinity to androgen receptor by fluorescence binding assay None 30.0 nM
Displacement of fluorescent-tagged R1881 from androgen receptor after 4 hrs by fluorometric assay None 29.0 nM
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 252.0 nM
DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 6.169 nM DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Mibolerone) Escherichia coli 4.112 nM
Displacement of [3H]R1881 from wild type human androgen receptor expressed in COS-1 cells co-transfected with pSG5 after 15 mins by scintillation assay relative to untreated control Homo sapiens 0.1 %
Displacement of [3H]R1881 from wild type human androgen receptor expressed in COS-1 cells co-transfected with pSG5 after 15 mins by scintillation assay Homo sapiens 4.571 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 33.2 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 37.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens -175.1 %
Displacement of [3H]Mibolerone from rat recombinant androgen receptor expressed in Escherichia coli after 4 hrs Rattus norvegicus 4.3 nM Displacement of [3H]Mibolerone from rat recombinant androgen receptor expressed in Escherichia coli after 4 hrs Rattus norvegicus 6.5 nM
Displacement of [3H]Mibolerone from rat recombinant androgen receptor expressed in Escherichia coli at 10 uM after 4 hrs relative to control Rattus norvegicus 2.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 79.99 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 92.19 %
Antagonist activity against pSG5-tagged human androgen receptor expressed in COS1 cells assessed as reduction in receptor-mediated transcriptional activity by AR-regulated rat probasin promoter fragment driven firefly luciferase reporter assay Homo sapiens 4.17 nM
Displacement of [3H]R1881 from pSG5-tagged human androgen receptor expressed in COS1 cells assessed as relative binding inhibition Homo sapiens 4.27 nM
Antagonist activity against pSG5-tagged human androgen receptor expressed in COS1 cells assessed as receptor-mediated testosterone-induced transcriptional activity at 10 uM by AR-regulated rat probasin promoter fragment driven firefly luciferase reporter assay (Rvb = 100 +/- 5.7%) Homo sapiens 100.0 %
Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in human embryonic kidney cells heterologically expressing alpha-1C subunit Homo sapiens 34.0 nM
Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in human embryonic kidney cells heterologically expressing alpha-1C subunit Homo sapiens 38.4 nM
Androgenic activity at human androgen receptor expressed in African green monkey CV-1 cells assessed as increase in interaction between VP16-fused AR-NTD and GAL4-fused AR-LBD after 17 hrs by luciferase reporter gene assay Homo sapiens 1.1 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -3.69 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -8.96 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 3.5 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa -7.2 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 8.83 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.12 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.59 %

Related Entries

Environmental Exposure

Countries
Malaysia
Vietnam

Cross References

Resources Reference
ChEBI 17347
ChEMBL CHEMBL386630
DrugBank DB00624
DrugCentral 2607
FDA SRS 3XMK78S47O
Guide to Pharmacology 2858
KEGG C00535
PDB TES
PharmGKB PA451627
PubChem 6013
SureChEMBL SCHEMBL8452
ZINC ZINC000118912393