5-[6-(3,5-Dihydroxy-4-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxybenzene-1,3-diol

Details

• Internal ID: 16815999-95f0-42e7-a06b-353f9bdfdd93
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 5-[6-(3,5-dihydroxy-4-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxybenzene-1,3-diol
• SMILES (Canonical): COC1=C(C=C(C=C1O)C2C3COC(C3CO2)C4=CC(=C(C(=C4)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1O)C2C3COC(C3CO2)C4=CC(=C(C(=C4)O)OC)O)O
• InChI: InChI=1S/C20H22O8/c1-25-19-13(21)3-9(4-14(19)22)17-11-7-28-18(12(11)8-27-17)10-5-15(23)20(26-2)16(24)6-10/h3-6,11-12,17-18,21-24H,7-8H2,1-2H3
• InChI Key: RYHHTEJSKIQZAS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.13146766 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9662	96.62%
Caco-2	+	0.5470	54.70%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9430	94.30%
OATP1B3 inhibitior	+	0.9543	95.43%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6006	60.06%
P-glycoprotein inhibitior	-	0.4875	48.75%
P-glycoprotein substrate	-	0.9636	96.36%
CYP3A4 substrate	-	0.5812	58.12%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	+	0.4564	45.64%
CYP3A4 inhibition	+	0.6560	65.60%
CYP2C9 inhibition	+	0.7142	71.42%
CYP2C19 inhibition	+	0.7431	74.31%
CYP2D6 inhibition	-	0.7075	70.75%
CYP1A2 inhibition	-	0.5070	50.70%
CYP2C8 inhibition	-	0.7602	76.02%
CYP inhibitory promiscuity	+	0.8933	89.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5263	52.63%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.6367	63.67%
Skin irritation	-	0.8180	81.80%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7818	78.18%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5425	54.25%
skin sensitisation	-	0.7476	74.76%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8939	89.39%
Acute Oral Toxicity (c)	III	0.6814	68.14%
Estrogen receptor binding	+	0.7143	71.43%
Androgen receptor binding	+	0.6401	64.01%
Thyroid receptor binding	+	0.5918	59.18%
Glucocorticoid receptor binding	+	0.6689	66.89%
Aromatase binding	-	0.5195	51.95%
PPAR gamma	+	0.6242	62.42%
Honey bee toxicity	-	0.9281	92.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9661	96.61%

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	98.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.95%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.57%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.61%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.45%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.10%	99.17%

Plants that contains it

• Lilium auratum

Cross-Links

• PubChem: 14284477
• LOTUS: LTS0264269
• wikiData: Q105247582