3-[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 40acf416-29a3-478c-a509-33c4f1075072
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 3-[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2COC(=O)C=CC3=CC(=C(C=C3)O)OC)C4=CC(=C(C(=C4)OC)O)OC)CCCOC(=O)C=CC5=CC(=C(C=C5)O)OC
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)C4=CC(=C(C(=C4)OC)O)OC)CCCOC(=O)/C=C/C5=CC(=C(C=C5)O)OC
• InChI: InChI=1S/C41H42O13/c1-47-32-18-24(8-12-30(32)42)10-14-37(44)52-16-6-7-26-17-28-29(23-53-38(45)15-11-25-9-13-31(43)33(19-25)48-2)40(54-41(28)36(20-26)51-5)27-21-34(49-3)39(46)35(22-27)50-4/h8-15,17-22,29,40,42-43,46H,6-7,16,23H2,1-5H3/b14-10+,15-11+/t29-,40+/m1/s1
• InChI Key: QJHLWANOBFZANN-BHVFZGEYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₂O₁₃
• Molecular Weight: 742.80 g/mol
• Exact Mass: 742.26254139 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 6.51
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	-	0.8543	85.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8315	83.15%
OATP2B1 inhibitior	+	0.5723	57.23%
OATP1B1 inhibitior	+	0.8083	80.83%
OATP1B3 inhibitior	+	0.8418	84.18%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9850	98.50%
P-glycoprotein inhibitior	+	0.8579	85.79%
P-glycoprotein substrate	-	0.5170	51.70%
CYP3A4 substrate	+	0.6797	67.97%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8104	81.04%
CYP3A4 inhibition	-	0.7013	70.13%
CYP2C9 inhibition	+	0.7726	77.26%
CYP2C19 inhibition	-	0.5190	51.90%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	-	0.6798	67.98%
CYP2C8 inhibition	+	0.9084	90.84%
CYP inhibitory promiscuity	+	0.6325	63.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4863	48.63%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.8775	87.75%
Skin corrosion	-	0.9604	96.04%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6898	68.98%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8108	81.08%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9232	92.32%
Acute Oral Toxicity (c)	III	0.5611	56.11%
Estrogen receptor binding	+	0.8414	84.14%
Androgen receptor binding	+	0.8254	82.54%
Thyroid receptor binding	+	0.6386	63.86%
Glucocorticoid receptor binding	+	0.8036	80.36%
Aromatase binding	+	0.6043	60.43%
PPAR gamma	+	0.7011	70.11%
Honey bee toxicity	-	0.8427	84.27%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9682	96.82%

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	98.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.76%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.59%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.36%	99.17%
CHEMBL3194	P02766	Transthyretin	94.43%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.40%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.79%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.44%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.22%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.46%	80.78%
CHEMBL1951	P21397	Monoamine oxidase A	85.58%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	84.48%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.35%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.07%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.82%	89.62%
CHEMBL5028	O14672	ADAM10	81.08%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.07%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.48%	97.09%

Plants that contains it

• Abelmoschus ficulneus
• Hibiscus cannabinus
• Ochroma pyramidale

Cross-Links

• PubChem: 101114360
• LOTUS: LTS0033479
• wikiData: Q105222677