(6alpha,11beta,16alpha)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

Details

• Internal ID: a0f88e17-6c36-4792-959a-25fb3d5e0f76
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: 12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
• SMILES (Canonical): CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)F)C
• SMILES (Isomeric): CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)F)C
• InChI: InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3
• InChI Key: FEBLZLNTKCEFIT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀F₂O₆
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.20104500 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Flucort
• Fluovitef
• Fluvean
• MFCD00010525
• 1262192-25-5
• N-Synalar (Salt/Mix)
• Neo-Synalar (Salt/Mix)
• MLS001196984
• SCHEMBL1276243
• 6.alpha.,9.alpha.-Difluoro-16.alpha.-hydroxyprednisolone 16,17-acetonide
• CHEMBL1599911
• DTXSID70859067
• FEBLZLNTKCEFIT-UHFFFAOYSA-N
• HMS2856O09
• (6alpha,9alpha,11beta,16beta)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
• 6.alpha.,9-Difluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone
• Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
• STL481763
• AKOS001650096
• AS-11053
• SMR000555611
• SY057543
• FT-0631295
• UNM000000588701
• (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9.0^{4,8.0^{13,18]icosa-14,17-dien-16-one
• (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
• (6.alpha.,11.beta.,16.alpha.)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
• (6.alpha.,11.beta.,16.alpha.)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidine)bis(oxy)]pregna-1,4-diene-3,20-dione
• 4b,12-Difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
• 4b,12-difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
• 4b,12-Difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one #
• Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,12-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6.alpha.,11.beta.,16.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	-	0.5910	59.10%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8220	82.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9626	96.26%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9324	93.24%
P-glycoprotein inhibitior	-	0.8681	86.81%
P-glycoprotein substrate	+	0.7777	77.77%
CYP3A4 substrate	+	0.7201	72.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8899	88.99%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9394	93.94%
CYP2C19 inhibition	-	0.9311	93.11%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.9327	93.27%
CYP2C8 inhibition	+	0.5748	57.48%
CYP inhibitory promiscuity	-	0.8806	88.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.7155	71.55%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9634	96.34%
Skin irritation	+	0.5577	55.77%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	+	0.5272	52.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7355	73.55%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.9875	98.75%
skin sensitisation	-	0.8597	85.97%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	I	0.6293	62.93%
Estrogen receptor binding	+	0.9184	91.84%
Androgen receptor binding	+	0.8718	87.18%
Thyroid receptor binding	+	0.7705	77.05%
Glucocorticoid receptor binding	+	0.8907	89.07%
Aromatase binding	+	0.9117	91.17%
PPAR gamma	-	0.5088	50.88%
Honey bee toxicity	-	0.7926	79.26%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9955	99.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	1.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	316.2 nM; 316.2 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.27%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	96.70%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.05%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	95.10%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.39%	100.00%
CHEMBL2034	P04150	Glucocorticoid receptor	93.58%	94.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.95%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.27%	95.56%
CHEMBL332	P03956	Matrix metalloproteinase-1	91.05%	94.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.43%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.27%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	89.12%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.26%	96.61%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.20%	86.92%
CHEMBL240	Q12809	HERG	87.99%	89.76%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.78%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.28%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.07%	95.50%
CHEMBL1871	P10275	Androgen Receptor	85.29%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.27%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.69%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.30%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.00%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.80%	94.45%

Plants that contains it

• Cinchona calisaya
• Paederia foetida
• Pyrus communis
• Rhododendron dauricum
• Senecio scandens
• Vaccinium vitis-idaea
• Xanthium spinosum subsp. spinosum

Cross-Links

• PubChem: 3381
• NPASS: NPC313528
• ChEMBL: CHEMBL1599911