(3E,4R)-3-(1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

Details

• Internal ID: 57b9071c-10d5-4ec5-a43d-a511eafbf742
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3E,4R)-3-(1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)CC2COC(=O)C2=CC3=CC4=C(C=C3)OCO4)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C[C@H]\2COC(=O)/C2=C/C3=CC4=C(C=C3)OCO4)OC
• InChI: InChI=1S/C21H20O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3/b16-8+/t15-/m0/s1
• InChI Key: GVNUFBXIXQNOCF-MDNIKOHYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.12598835 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 50816-74-5
• FS-8148

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.7793	77.93%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7603	76.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9216	92.16%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9338	93.38%
P-glycoprotein inhibitior	+	0.8449	84.49%
P-glycoprotein substrate	-	0.7060	70.60%
CYP3A4 substrate	+	0.5932	59.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7972	79.72%
CYP3A4 inhibition	+	0.9591	95.91%
CYP2C9 inhibition	+	0.9399	93.99%
CYP2C19 inhibition	+	0.9801	98.01%
CYP2D6 inhibition	+	0.8096	80.96%
CYP1A2 inhibition	+	0.6598	65.98%
CYP2C8 inhibition	+	0.5194	51.94%
CYP inhibitory promiscuity	+	0.9845	98.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4437	44.37%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.8660	86.60%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8295	82.95%
Micronuclear	+	0.6874	68.74%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	+	0.5463	54.63%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5644	56.44%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.8587	85.87%
Androgen receptor binding	+	0.6592	65.92%
Thyroid receptor binding	+	0.7345	73.45%
Glucocorticoid receptor binding	+	0.7256	72.56%
Aromatase binding	-	0.6493	64.93%
PPAR gamma	+	0.6466	64.66%
Honey bee toxicity	-	0.7693	76.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9897	98.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.21%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.60%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.14%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.07%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.02%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.09%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.09%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.05%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.84%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.77%	95.89%
CHEMBL2535	P11166	Glucose transporter	87.92%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.69%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.98%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.63%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.41%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.85%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.66%	96.77%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.99%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.94%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.34%	93.00%
CHEMBL2039	P27338	Monoamine oxidase B	81.78%	92.51%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.77%	92.38%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.63%	97.50%

Plants that contains it

• Philotheca fitzgeraldii
• Taxus baccata

Cross-Links

• PubChem: 132350840
• LOTUS: LTS0146837
• wikiData: Q105021460