5-{2-Fluoro-5-[3-(3-hydroxy-2-methoxycarbonyl-phenoxy)-propenyl]-phenyl}-isoxazole-3-carboxylic acid

Details

• Internal ID: 41bdd2fe-c9f4-469a-97f3-5916036235f4
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters > o-Hydroxybenzoic acid esters
• IUPAC Name: 5-[2-fluoro-5-[(E)-3-(3-hydroxy-2-methoxycarbonylphenoxy)prop-1-enyl]phenyl]-1,2-oxazole-3-carboxylic acid
• SMILES (Canonical): COC(=O)C1=C(C=CC=C1OCC=CC2=CC(=C(C=C2)F)C3=CC(=NO3)C(=O)O)O
• SMILES (Isomeric): COC(=O)C1=C(C=CC=C1OC/C=C/C2=CC(=C(C=C2)F)C3=CC(=NO3)C(=O)O)O
• InChI: InChI=1S/C21H16FNO7/c1-28-21(27)19-16(24)5-2-6-17(19)29-9-3-4-12-7-8-14(22)13(10-12)18-11-15(20(25)26)23-30-18/h2-8,10-11,24H,9H2,1H3,(H,25,26)/b4-3+
• InChI Key: QKHWJUMLYAYZFS-ONEGZZNKSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆FNO₇
• Molecular Weight: 413.40 g/mol
• Exact Mass: 413.09108001 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 5-{2-FLUORO-5-[3-(3-HYDROXY-2-METHOXYCARBONYL-PHENOXY)-PROPENYL]-PHENYL}-ISOXAZOLE-3-CARBOXYLIC ACID
• CHEMBL117869
• 1q1m
• SCHEMBL5620738
• SCHEMBL5620749
• BDBM13990
• DB02014
• PD008221
• Q27093104
• 5-(2-Fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]-1-propen-1-yl}phenyl)-1,2-oxazole-3-carboxylic acid
• 5-(2-fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl}phenyl)isoxazole-3-carboxylic acid
• 5-{2-fluoro-5-[(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl]phenyl}-1,2-oxazole-3-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.7376	73.76%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7104	71.04%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.8855	88.55%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9531	95.31%
P-glycoprotein inhibitior	+	0.7772	77.72%
P-glycoprotein substrate	-	0.5696	56.96%
CYP3A4 substrate	+	0.6283	62.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8829	88.29%
CYP3A4 inhibition	-	0.5830	58.30%
CYP2C9 inhibition	+	0.6453	64.53%
CYP2C19 inhibition	+	0.6329	63.29%
CYP2D6 inhibition	-	0.8830	88.30%
CYP1A2 inhibition	+	0.5936	59.36%
CYP2C8 inhibition	+	0.9031	90.31%
CYP inhibitory promiscuity	+	0.7756	77.56%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7943	79.43%
Carcinogenicity (trinary)	Non-required	0.4031	40.31%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9346	93.46%
Skin irritation	-	0.8389	83.89%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7313	73.13%
Micronuclear	+	0.7748	77.48%
Hepatotoxicity	+	0.5929	59.29%
skin sensitisation	-	0.8637	86.37%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5990	59.90%
Acute Oral Toxicity (c)	III	0.6760	67.60%
Estrogen receptor binding	+	0.8021	80.21%
Androgen receptor binding	+	0.8563	85.63%
Thyroid receptor binding	+	0.6286	62.86%
Glucocorticoid receptor binding	+	0.8702	87.02%
Aromatase binding	+	0.6531	65.31%
PPAR gamma	+	0.8609	86.09%
Honey bee toxicity	-	0.9219	92.19%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9788	97.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.06%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.57%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.41%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.86%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.80%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.74%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	93.64%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	91.76%	91.49%
CHEMBL2535	P11166	Glucose transporter	91.19%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.17%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.03%	87.67%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.11%	81.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.04%	96.95%
CHEMBL3194	P02766	Transthyretin	85.63%	90.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.62%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.89%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.59%	98.95%
CHEMBL1811	P34995	Prostanoid EP1 receptor	84.52%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.50%	91.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.26%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.34%	90.24%

Plants that contains it

• Chrysothamnus viscidiflorus

Cross-Links

• PubChem: 447994
• LOTUS: LTS0236660
• wikiData: Q27093104