(5R,5aS,8aR)-5-(1,3-benzodioxol-5-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	4447c0a3-9f87-47e0-92d7-3e7465994267
Taxonomy	Lignans, neolignans and related compounds > Lignan lactones
IUPAC Name	(5R,5aS,8aR)-5-(1,3-benzodioxol-5-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
SMILES (Canonical)	C1C2COC(=O)C2C(C3=CC4=C(C=C31)OCO4)C5=CC6=C(C=C5)OCO6
SMILES (Isomeric)	C1[C@H]2COC(=O)[C@H]2[C@@H](C3=CC4=C(C=C31)OCO4)C5=CC6=C(C=C5)OCO6
InChI	InChI=1S/C20H16O6/c21-20-19-12(7-22-20)3-11-5-16-17(26-9-25-16)6-13(11)18(19)10-1-2-14-15(4-10)24-8-23-14/h1-2,4-6,12,18-19H,3,7-9H2/t12-,18+,19+/m0/s1
InChI Key	SCTKDFCQZSBHEE-GESALYCCSA-N
Popularity	2 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₆O₆
Molecular Weight	352.30 g/mol
Exact Mass	352.09468823 g/mol
Topological Polar Surface Area (TPSA)	63.20 Å²
XlogP	3.20
Atomic LogP (AlogP)	2.62
H-Bond Acceptor	6
H-Bond Donor	0
Rotatable Bonds	1

Synonyms

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(5R,5aS,8aR)-5-(1,3-benzodioxol-5-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.6891	68.91%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7512	75.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9164	91.64%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8731	87.31%
P-glycoprotein inhibitior	+	0.6164	61.64%
P-glycoprotein substrate	-	0.9218	92.18%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	+	0.5975	59.75%
CYP2D6 substrate	-	0.7917	79.17%
CYP3A4 inhibition	+	0.7711	77.11%
CYP2C9 inhibition	+	0.8494	84.94%
CYP2C19 inhibition	+	0.8099	80.99%
CYP2D6 inhibition	+	0.6366	63.66%
CYP1A2 inhibition	+	0.8281	82.81%
CYP2C8 inhibition	-	0.8866	88.66%
CYP inhibitory promiscuity	+	0.8494	84.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Warning	0.4785	47.85%
Eye corrosion	-	0.9753	97.53%
Eye irritation	-	0.6689	66.89%
Skin irritation	-	0.6039	60.39%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3729	37.29%
Micronuclear	+	0.7774	77.74%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.6613	66.13%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.8621	86.21%
Acute Oral Toxicity (c)	III	0.7249	72.49%
Estrogen receptor binding	+	0.8414	84.14%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	+	0.6272	62.72%
Glucocorticoid receptor binding	+	0.5753	57.53%
Aromatase binding	+	0.5628	56.28%
PPAR gamma	+	0.6401	64.01%
Honey bee toxicity	-	0.8020	80.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9670	96.70%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	97.16%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.97%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.95%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.56%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.18%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.92%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.19%	83.82%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.91%	93.40%
CHEMBL2581	P07339	Cathepsin D	85.72%	98.95%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.46%	80.96%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.16%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.27%	96.77%
CHEMBL2039	P27338	Monoamine oxidase B	82.64%	92.51%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.04%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.81%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.81%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.71%	92.62%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.