5-[(3S,3aR,6R,6aR)-6-[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole

Details

• Internal ID: de54a8b0-b31b-4292-9fdb-cf86f073dd40
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 5-[(3S,3aR,6R,6aR)-6-[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
• SMILES (Canonical): CC(=CCOC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)OC)C
• SMILES (Isomeric): CC(=CCOC1=C(C=C(C=C1)[C@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC5=C(C=C4)OCO5)OC)C
• InChI: InChI=1S/C25H28O6/c1-15(2)8-9-27-20-6-4-16(10-22(20)26-3)24-18-12-29-25(19(18)13-28-24)17-5-7-21-23(11-17)31-14-30-21/h4-8,10-11,18-19,24-25H,9,12-14H2,1-3H3/t18-,19-,24-,25+/m0/s1
• InChI Key: WXYFFRZGPDZASV-QXVOXHNYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.84
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.5784	57.84%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7601	76.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9178	91.78%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9661	96.61%
P-glycoprotein inhibitior	+	0.8928	89.28%
P-glycoprotein substrate	-	0.8142	81.42%
CYP3A4 substrate	+	0.5624	56.24%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.7100	71.00%
CYP3A4 inhibition	+	0.9219	92.19%
CYP2C9 inhibition	+	0.7372	73.72%
CYP2C19 inhibition	+	0.9131	91.31%
CYP2D6 inhibition	-	0.5679	56.79%
CYP1A2 inhibition	+	0.5897	58.97%
CYP2C8 inhibition	+	0.4695	46.95%
CYP inhibitory promiscuity	+	0.9571	95.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9608	96.08%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9315	93.15%
Skin irritation	-	0.8152	81.52%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9330	93.30%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6564	65.64%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7700	77.00%
Acute Oral Toxicity (c)	III	0.5893	58.93%
Estrogen receptor binding	+	0.7661	76.61%
Androgen receptor binding	+	0.7596	75.96%
Thyroid receptor binding	+	0.6317	63.17%
Glucocorticoid receptor binding	+	0.7335	73.35%
Aromatase binding	-	0.5103	51.03%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.8393	83.93%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.12%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.24%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.97%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.51%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.88%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.56%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.43%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.76%	96.00%
CHEMBL2581	P07339	Cathepsin D	86.96%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.87%	85.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.88%	98.75%
CHEMBL4208	P20618	Proteasome component C5	84.93%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.54%	94.73%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.44%	89.44%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.98%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.90%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.67%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.15%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.99%	94.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.50%	89.67%
CHEMBL240	Q12809	HERG	81.46%	89.76%

Plants that contains it

• Zanthoxylum dimorphophyllum

Cross-Links

• PubChem: 162902550
• LOTUS: LTS0171435
• wikiData: Q105321957