Structure

InChI Key YNDXUCZADRHECN-JNQJZLCISA-N
Smiles CC1(C)O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
InChI
InChI=1S/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H31FO6
Molecular Weight 434.5
AlogP 2.42
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 93.06
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Glucocorticoid receptor agonist AGONIST DailyMed Wikipedia Wikipedia
Protein: Glucocorticoid receptor

Description: Glucocorticoid receptor

Organism : Homo sapiens

P04150 ENSG00000113580
Assay Description Organism Bioactivity Reference
Maximal percent of fibroblast cell growth inhibition using antiproliferative assay Mus musculus 25.0 %
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 179.0 nM DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 23.0 nM
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 4.414 nM DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 2.006 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 128.12 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 115.53 %
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 7.65 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.69 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 14.59 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 16.43 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 28.78 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.96 %
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 -5.82 %

Related Entries

Cross References

Resources Reference
ChEBI 71418
ChEMBL CHEMBL1504
DrugCentral 2726
FDA SRS F446C597KA
Guide to Pharmacology 2867
KEGG C08183
PDB 1TA
PubChem 6436
SureChEMBL SCHEMBL4689
ZINC ZINC000003875481