(3E,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(4-hydroxy-3-methoxyphenyl)methylidene]oxolan-2-one

Details

• Internal ID: b901fb51-6a18-4632-8832-b0474194bbe1
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3E,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(4-hydroxy-3-methoxyphenyl)methylidene]oxolan-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C=C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/2\[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4)O
• InChI: InChI=1S/C20H18O6/c1-23-18-8-13(2-4-16(18)21)7-15-14(10-24-20(15)22)6-12-3-5-17-19(9-12)26-11-25-17/h2-5,7-9,14,21H,6,10-11H2,1H3/b15-7+/t14-/m0/s1
• InChI Key: PYINQNNZGBAXJN-UUINEXAVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.93
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.5271	52.71%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8093	80.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9241	92.41%
OATP1B3 inhibitior	+	0.9673	96.73%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8921	89.21%
P-glycoprotein inhibitior	-	0.4576	45.76%
P-glycoprotein substrate	-	0.8055	80.55%
CYP3A4 substrate	+	0.5741	57.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7969	79.69%
CYP3A4 inhibition	+	0.8876	88.76%
CYP2C9 inhibition	+	0.9332	93.32%
CYP2C19 inhibition	+	0.9362	93.62%
CYP2D6 inhibition	+	0.7075	70.75%
CYP1A2 inhibition	+	0.6034	60.34%
CYP2C8 inhibition	+	0.5347	53.47%
CYP inhibitory promiscuity	+	0.9431	94.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.4060	40.60%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.8468	84.68%
Skin irritation	-	0.7362	73.62%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4056	40.56%
Micronuclear	+	0.7474	74.74%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.5616	56.16%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6711	67.11%
Acute Oral Toxicity (c)	III	0.5996	59.96%
Estrogen receptor binding	+	0.9231	92.31%
Androgen receptor binding	+	0.6910	69.10%
Thyroid receptor binding	+	0.6574	65.74%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	-	0.4847	48.47%
PPAR gamma	+	0.8177	81.77%
Honey bee toxicity	-	0.8241	82.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9821	98.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.88%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.64%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.75%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.48%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.63%	94.80%
CHEMBL1951	P21397	Monoamine oxidase A	91.00%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.73%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.83%	96.77%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.81%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.61%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.53%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.97%	95.89%
CHEMBL2535	P11166	Glucose transporter	86.89%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.59%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.21%	85.14%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.17%	80.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.49%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.53%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.70%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.49%	97.14%

Plants that contains it

• Taiwania cryptomerioides

Cross-Links

• PubChem: 163186855
• LOTUS: LTS0202465
• wikiData: Q105216598