(3R,3aS,6S,6aR)-3,6-bis(1,3-benzodioxol-5-yl)-1,4,6,6a-tetrahydrofuro[3,4-c]furan-3,3a-diol

Details

• Internal ID: 78d1de8d-5ac7-4d7f-b0b9-95917b2ce36a
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: (3R,3aS,6S,6aR)-3,6-bis(1,3-benzodioxol-5-yl)-1,4,6,6a-tetrahydrofuro[3,4-c]furan-3,3a-diol
• SMILES (Canonical): C1C2C(OCC2(C(O1)(C3=CC4=C(C=C3)OCO4)O)O)C5=CC6=C(C=C5)OCO6
• SMILES (Isomeric): C1[C@@H]2[C@H](OC[C@@]2([C@](O1)(C3=CC4=C(C=C3)OCO4)O)O)C5=CC6=C(C=C5)OCO6
• InChI: InChI=1S/C20H18O8/c21-19-8-23-18(11-1-3-14-16(5-11)26-9-24-14)13(19)7-28-20(19,22)12-2-4-15-17(6-12)27-10-25-15/h1-6,13,18,21-22H,7-10H2/t13-,18-,19-,20-/m1/s1
• InChI Key: WQZHIPWFEKLEJM-WNISUXOKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.10016753 g/mol
• Topological Polar Surface Area (TPSA): 95.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9397	93.97%
Caco-2	-	0.6854	68.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7610	76.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9212	92.12%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7178	71.78%
P-glycoprotein inhibitior	+	0.5814	58.14%
P-glycoprotein substrate	-	0.8927	89.27%
CYP3A4 substrate	+	0.5083	50.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.7571	75.71%
CYP2C9 inhibition	-	0.7828	78.28%
CYP2C19 inhibition	-	0.6064	60.64%
CYP2D6 inhibition	-	0.8161	81.61%
CYP1A2 inhibition	-	0.8533	85.33%
CYP2C8 inhibition	-	0.8050	80.50%
CYP inhibitory promiscuity	-	0.8726	87.26%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4049	40.49%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.7958	79.58%
Skin irritation	-	0.7760	77.60%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6186	61.86%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.7045	70.45%
skin sensitisation	-	0.8535	85.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6541	65.41%
Acute Oral Toxicity (c)	III	0.5357	53.57%
Estrogen receptor binding	+	0.8784	87.84%
Androgen receptor binding	+	0.7708	77.08%
Thyroid receptor binding	+	0.7060	70.60%
Glucocorticoid receptor binding	+	0.6441	64.41%
Aromatase binding	+	0.6443	64.43%
PPAR gamma	+	0.8053	80.53%
Honey bee toxicity	-	0.7324	73.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9712	97.12%

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	99.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.70%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.25%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.53%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.42%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.52%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.49%	96.77%
CHEMBL1951	P21397	Monoamine oxidase A	87.47%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.93%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.93%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.76%	95.56%

Plants that contains it

• Gmelina arborea

Cross-Links

• PubChem: 162910976
• LOTUS: LTS0269369
• wikiData: Q105311109