Pleconaril

Details

• Internal ID: e2df981b-004a-4cd5-983e-f3fd9c81028c
• Taxonomy: Organoheterocyclic compounds > Azoles > Oxadiazoles > 1,2,4-oxadiazoles > Phenyloxadiazoles
• IUPAC Name: 3-[3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
• SMILES (Canonical): CC1=CC(=CC(=C1OCCCC2=CC(=NO2)C)C)C3=NOC(=N3)C(F)(F)F
• SMILES (Isomeric): CC1=CC(=CC(=C1OCCCC2=CC(=NO2)C)C)C3=NOC(=N3)C(F)(F)F
• InChI: InChI=1S/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3
• InChI Key: KQOXLKOJHVFTRN-UHFFFAOYSA-N
• Popularity: 473 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈F₃N₃O₃
• Molecular Weight: 381.30 g/mol
• Exact Mass: 381.13002593 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 153168-05-9
• Picovir
• Win-63843
• Win 63843
• Pleconaril-d8
• VP-63843
• VP 63843
• Pleconaril [USAN:INN]
• 3-(3,5-dimethyl-4-(3-(3-methylisoxazol-5-yl)propoxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
• 3-[3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
• 3-{3,5-dimethyl-4-[3-(3-methyl-isoxazol-5-yl)-propoxy]-phenyl}-5-trifluoromethyl-[1,2,4]oxadiazole
• CHEMBL29609
• DTXSID8057649
• UNII-9H4570Q89D
• C18H18F3N3O3
• 9H4570Q89D
• SR-63843
• SR-263843
• 3-(4-(3-(3-Methyl-5-isoxazolyl)propoxy)-3,5-xylyl)-5-trifluoromethyl)-1,2,4-oxadizole
• 3-(3,5-Dimethyl-4-(3-(3-methyl-5-isoxazolyl)propoxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
• 3-[3,5-Dimethyl-4-[3-(3-methyl-5-isoxazolyl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
• 3-[3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
• 1,2,4-Oxadiazole, 3-(3,5-dimethyl-4-(3-(3-methyl-5-isoxazolyl)propoxy)phenyl)-5-(trifluoromethyl)-
• 5-[3-[2,6-dimethyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]propyl]-3-methylisoxazole
• W11
• Pleconarilis
• 3-(3,5-dimethyl-4-(3-(3-methyl-1,2-oxazol-5-yl)propoxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
• 3-(3,5-Dimethyl-4-[3-(3-methylisoxazol-5-yl)Propoxy]Phenyl)-5-(Trifluoromethyl)-1,2,4-Oxadiazole
• WIN63843
• Pleconaril < Prop INN
• PLECONARIL [MI]
• PLECONARIL [INN]
• Pleconaril (USAN/INN)
• PLECONARIL [USAN]
• D0W1US
• PLECONARIL [MART.]
• PLECONARIL [WHO-DD]
• SCHEMBL49383
• DTXCID9031438
• Pleconaril, >=98% (HPLC)
• KQOXLKOJHVFTRN-UHFFFAOYSA-N
• BCP20819
• EX-A1448
• Tox21_113756
• BDBM50111469
• MFCD00923611
• AKOS016005860
• Pleconaril;VP 63843;Win 63843
• C18-H18-F3-N3-O3
• CS-5475
• DB05105
• VP63843
• NCGC00253627-01
• 3-(3,5-dimethyl-4((3-(3-methyl-5-isoxazolyl)propyl)phenyl)-5-trifluoromethyl)-1,2,4-oxadiazole
• AC-36849
• AS-77268
• HY-19952
• Pleconaril 100 microg/mL in Acetonitrile
• LS-173443
• CAS-153168-05-9
• FT-0673964
• FT-0673965
• D05528
• F20826
• A847822
• Q770293
• SR-01000945059
• J-008988
• SR-01000945059-1
• 1,3-Dimethyl-2-[3-(3-methylisoxazol-5-yl)propoxy]-5-[5-(trifluoromethyl)(1,2,4-oxadiazol-3-yl)]benzene
• 3-{3,5-Dimethyl-4-[3-(3-methyl-isoxazol-5-yl)-propoxy]-phenyl}-5-trifluoromethyl-[1,2,4]oxadiazole(Pleconaril)
• Pleconaril3-{3,5-Dimethyl-4-[3-(3-methyl-isoxazol-5-yl)-propoxy]-phenyl}-5-trifluoromethyl-[1,2,4]oxadiazole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	-	0.5356	53.56%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7970	79.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9034	90.34%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8542	85.42%
P-glycoprotein inhibitior	+	0.5931	59.31%
P-glycoprotein substrate	-	0.5253	52.53%
CYP3A4 substrate	+	0.5920	59.20%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.7649	76.49%
CYP3A4 inhibition	-	0.6775	67.75%
CYP2C9 inhibition	-	0.5778	57.78%
CYP2C19 inhibition	+	0.7046	70.46%
CYP2D6 inhibition	-	0.8948	89.48%
CYP1A2 inhibition	+	0.6447	64.47%
CYP2C8 inhibition	+	0.8879	88.79%
CYP inhibitory promiscuity	+	0.7105	71.05%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.4986	49.86%
Eye corrosion	-	0.9805	98.05%
Eye irritation	-	0.8854	88.54%
Skin irritation	-	0.8096	80.96%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9037	90.37%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8379	83.79%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5208	52.08%
Acute Oral Toxicity (c)	III	0.5111	51.11%
Estrogen receptor binding	+	0.8015	80.15%
Androgen receptor binding	+	0.5993	59.93%
Thyroid receptor binding	+	0.6463	64.63%
Glucocorticoid receptor binding	+	0.6056	60.56%
Aromatase binding	+	0.7076	70.76%
PPAR gamma	+	0.6315	63.15%
Honey bee toxicity	-	0.9177	91.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6441	64.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	1258.93 nM	IC50	PMID: 21986585
CHEMBL340	P08684	Cytochrome P450 3A4	6309.57 nM	IC50	PMID: 21986585
CHEMBL3401	O75469	Pregnane X receptor	251.19 nM; 251.19 nM	EC50; EC50	PMID: 22194678; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3524	P56524	Histone deacetylase 4	99.33%	92.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.76%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.31%	99.17%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	94.94%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.20%	94.00%
CHEMBL2039	P27338	Monoamine oxidase B	92.76%	92.51%
CHEMBL4302	P08183	P-glycoprotein 1	90.40%	92.98%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.93%	95.78%
CHEMBL230	P35354	Cyclooxygenase-2	88.98%	89.63%
CHEMBL240	Q12809	HERG	88.24%	89.76%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.14%	99.15%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.63%	89.67%
CHEMBL2581	P07339	Cathepsin D	86.46%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.86%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.51%	92.94%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.36%	89.44%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.65%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.39%	96.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.33%	97.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.12%	80.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.41%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.18%	96.90%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.04%	91.11%
CHEMBL1907	P15144	Aminopeptidase N	80.54%	93.31%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 1684
• NPASS: NPC471615
• ChEMBL: CHEMBL29609
• LOTUS: LTS0217224
• wikiData: Q770293