4-[(3R,3aS,6R,6aS)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenol

Details

• Internal ID: c2c2c37e-44c6-4702-b637-2cfae22cbc40
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[(3R,3aS,6R,6aS)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC5=C(C=C4)OCO5)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@H]3CO[C@H]([C@@H]3CO2)C4=CC5=C(C=C4)OCO5)O
• InChI: InChI=1S/C20H20O6/c1-22-17-6-11(2-4-15(17)21)19-13-8-24-20(14(13)9-23-19)12-3-5-16-18(7-12)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3/t13-,14-,19+,20+/m1/s1
• InChI Key: VBIRCRCPHNUJAS-NSMLZSOPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.12598835 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEMBL2011540
• 52151-92-5
• BDBM50379798
• 54983-96-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	+	0.5751	57.51%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7761	77.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9299	92.99%
OATP1B3 inhibitior	+	0.9781	97.81%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7034	70.34%
P-glycoprotein inhibitior	+	0.6297	62.97%
P-glycoprotein substrate	-	0.9523	95.23%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	+	0.3482	34.82%
CYP3A4 inhibition	+	0.8633	86.33%
CYP2C9 inhibition	+	0.8843	88.43%
CYP2C19 inhibition	+	0.9027	90.27%
CYP2D6 inhibition	+	0.6363	63.63%
CYP1A2 inhibition	+	0.5997	59.97%
CYP2C8 inhibition	-	0.6414	64.14%
CYP inhibitory promiscuity	+	0.8730	87.30%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9008	90.08%
Carcinogenicity (trinary)	Warning	0.3743	37.43%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.7972	79.72%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7611	76.11%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7412	74.12%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7609	76.09%
Acute Oral Toxicity (c)	III	0.6513	65.13%
Estrogen receptor binding	+	0.8249	82.49%
Androgen receptor binding	+	0.7789	77.89%
Thyroid receptor binding	+	0.6765	67.65%
Glucocorticoid receptor binding	+	0.6679	66.79%
Aromatase binding	-	0.5449	54.49%
PPAR gamma	+	0.6631	66.31%
Honey bee toxicity	-	0.8745	87.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9790	97.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	33900 nM	EC50	PMID: 22381047
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	18900 nM	EC50	PMID: 22381047

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.54%	85.14%
CHEMBL3438	Q05513	Protein kinase C zeta	92.43%	88.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.87%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.36%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.97%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.51%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.02%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.81%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.28%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.18%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.41%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.05%	99.15%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.90%	82.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.92%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.69%	96.77%
CHEMBL4208	P20618	Proteasome component C5	80.97%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.93%	92.94%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Artemisia argyi
• Artemisia montana
• Artemisia princeps
• Asarum heterotropoides
• Asarum sieboldii
• Beaucarnea recurvata
• Centaurea arenaria
• Citrus maxima
• Cotylelobium scabriusculum
• Cratystylis conocephala
• Diospyros abyssinica
• Diospyros elliptifolia
• Diospyros malabarica
• Gutenbergia cordifolia
• Magnolia stellata
• Mikania scandens
• Myristica fragrans
• Phyllodium pulchellum
• Scorzonera hispanica
• Sesamum indicum
• Trapa natans var. japonica
• Vitex negundo
• Zanthoxylum bungeanum
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 70695728
• NPASS: NPC123526
• ChEMBL: CHEMBL2011540
• LOTUS: LTS0073999
• wikiData: Q105283258