[(5R,5aR,8aS)-8a-hydroxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate

Details

• Internal ID: 7487890d-ac5c-46af-9682-08a72125f669
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: [(5R,5aR,8aS)-8a-hydroxy-6-oxo-5-(3,4,5-trimethoxyphenyl)-8,9-dihydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate
• SMILES (Canonical): CC(=O)OC12C(C3=CC4=C(C=C3CC1(COC2=O)O)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• SMILES (Isomeric): CC(=O)O[C@]12[C@@H](C3=CC4=C(C=C3C[C@@]1(COC2=O)O)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• InChI: InChI=1S/C24H24O10/c1-12(25)34-24-20(13-5-18(28-2)21(30-4)19(6-13)29-3)15-8-17-16(32-11-33-17)7-14(15)9-23(24,27)10-31-22(24)26/h5-8,20,27H,9-11H2,1-4H3/t20-,23+,24+/m1/s1
• InChI Key: POIAZYKALWSBHF-QDSKXPNFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₁₀
• Molecular Weight: 472.40 g/mol
• Exact Mass: 472.13694696 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.6032	60.32%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7265	72.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9380	93.80%
P-glycoprotein inhibitior	+	0.7812	78.12%
P-glycoprotein substrate	-	0.7614	76.14%
CYP3A4 substrate	+	0.6499	64.99%
CYP2C9 substrate	-	0.7923	79.23%
CYP2D6 substrate	-	0.8454	84.54%
CYP3A4 inhibition	+	0.6915	69.15%
CYP2C9 inhibition	+	0.5113	51.13%
CYP2C19 inhibition	-	0.7107	71.07%
CYP2D6 inhibition	-	0.8959	89.59%
CYP1A2 inhibition	-	0.9523	95.23%
CYP2C8 inhibition	+	0.4500	45.00%
CYP inhibitory promiscuity	-	0.6876	68.76%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.3740	37.40%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8656	86.56%
Skin irritation	-	0.8319	83.19%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4354	43.54%
Micronuclear	+	0.7733	77.33%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.7520	75.20%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.7467	74.67%
Acute Oral Toxicity (c)	III	0.5694	56.94%
Estrogen receptor binding	+	0.9027	90.27%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	+	0.7012	70.12%
Glucocorticoid receptor binding	+	0.8202	82.02%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7636	76.36%
Honey bee toxicity	-	0.7153	71.53%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9115	91.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.72%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.59%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.57%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.32%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.96%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.33%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.92%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.11%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.38%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.07%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.84%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.22%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.03%	89.50%
CHEMBL4208	P20618	Proteasome component C5	85.86%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.81%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	84.15%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.61%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.58%	100.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.99%	82.67%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.06%	80.96%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.46%	96.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.24%	94.00%

Plants that contains it

• Commiphora erlangeriana

Cross-Links

• PubChem: 10863670
• LOTUS: LTS0017878
• wikiData: Q105212418