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

Details

• Internal ID: 2472d146-a110-42df-bb09-e0471c4356a3
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: [(5R,5aR,8aS)-6-oxo-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[6,5-f][1,3]benzodioxol-5a-yl] acetate
• SMILES (Canonical): CC(=O)OC12C(CC3=CC4=C(C=C3C1C5=CC(=C(C(=C5)OC)OC)OC)OCO4)COC2=O
• SMILES (Isomeric): CC(=O)O[C@@]12[C@@H](CC3=CC4=C(C=C3[C@H]1C5=CC(=C(C(=C5)OC)OC)OC)OCO4)COC2=O
• InChI: InChI=1S/C24H24O9/c1-12(25)33-24-15(10-30-23(24)26)5-13-6-17-18(32-11-31-17)9-16(13)21(24)14-7-19(27-2)22(29-4)20(8-14)28-3/h6-9,15,21H,5,10-11H2,1-4H3/t15-,21+,24-/m0/s1
• InChI Key: BHVAPNQLLDELLV-HXKVFGNASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₉
• Molecular Weight: 456.40 g/mol
• Exact Mass: 456.14203234 g/mol
• Topological Polar Surface Area (TPSA): 98.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.6462	64.62%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7226	72.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9681	96.81%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9629	96.29%
P-glycoprotein inhibitior	+	0.8143	81.43%
P-glycoprotein substrate	-	0.8040	80.40%
CYP3A4 substrate	+	0.6440	64.40%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8335	83.35%
CYP3A4 inhibition	+	0.8751	87.51%
CYP2C9 inhibition	+	0.7962	79.62%
CYP2C19 inhibition	+	0.7353	73.53%
CYP2D6 inhibition	-	0.8692	86.92%
CYP1A2 inhibition	-	0.9021	90.21%
CYP2C8 inhibition	-	0.6280	62.80%
CYP inhibitory promiscuity	+	0.8025	80.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Non-required	0.3763	37.63%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.8905	89.05%
Skin irritation	-	0.8412	84.12%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7718	77.18%
Micronuclear	+	0.7474	74.74%
Hepatotoxicity	+	0.6177	61.77%
skin sensitisation	-	0.7055	70.55%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5305	53.05%
Acute Oral Toxicity (c)	III	0.6387	63.87%
Estrogen receptor binding	+	0.9175	91.75%
Androgen receptor binding	+	0.6727	67.27%
Thyroid receptor binding	+	0.7329	73.29%
Glucocorticoid receptor binding	+	0.8855	88.55%
Aromatase binding	-	0.5678	56.78%
PPAR gamma	+	0.7648	76.48%
Honey bee toxicity	-	0.6871	68.71%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9778	97.78%

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	99.63%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	98.66%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.37%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.88%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.36%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.56%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.34%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.21%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.73%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.58%	95.89%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.55%	80.96%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.90%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.87%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.72%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.20%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.40%	91.19%
CHEMBL4208	P20618	Proteasome component C5	82.36%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.23%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.56%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	81.40%	96.76%
CHEMBL2535	P11166	Glucose transporter	80.50%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.21%	99.17%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.01%	82.67%

Plants that contains it

• Commiphora erlangeriana

Cross-Links

• PubChem: 11004967
• LOTUS: LTS0011091
• wikiData: Q104936246