methyl (2R,3R)-2-(3,4-dihydroxyphenyl)-4-[(E)-3-[(2R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy-3-oxoprop-1-enyl]-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate

Details

• Internal ID: 4a3e84de-b8d8-4f32-9442-ae91eac3d396
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: methyl (2R,3R)-2-(3,4-dihydroxyphenyl)-4-[(E)-3-[(2R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy-3-oxoprop-1-enyl]-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate
• SMILES (Canonical): COC(=O)C1C(OC2=C(C=CC(=C12)C=CC(=O)OC(CC3=CC(=C(C=C3)O)O)C(=O)OC)O)C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): COC(=O)[C@H]1[C@@H](OC2=C(C=CC(=C12)/C=C/C(=O)O[C@H](CC3=CC(=C(C=C3)O)O)C(=O)OC)O)C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C29H26O12/c1-38-28(36)22(12-14-3-7-17(30)20(33)11-14)40-23(35)10-6-15-4-9-19(32)27-24(15)25(29(37)39-2)26(41-27)16-5-8-18(31)21(34)13-16/h3-11,13,22,25-26,30-34H,12H2,1-2H3/b10-6+/t22-,25-,26+/m1/s1
• InChI Key: YAXTXMBBIHBGPZ-QQJQYKEBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₆O₁₂
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.14242626 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9244	92.44%
Caco-2	-	0.8588	85.88%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7452	74.52%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.8831	88.31%
OATP1B3 inhibitior	+	0.8961	89.61%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9041	90.41%
P-glycoprotein inhibitior	+	0.7869	78.69%
P-glycoprotein substrate	-	0.5307	53.07%
CYP3A4 substrate	+	0.6747	67.47%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8225	82.25%
CYP3A4 inhibition	-	0.6049	60.49%
CYP2C9 inhibition	+	0.7664	76.64%
CYP2C19 inhibition	+	0.5193	51.93%
CYP2D6 inhibition	-	0.8585	85.85%
CYP1A2 inhibition	-	0.6593	65.93%
CYP2C8 inhibition	+	0.7649	76.49%
CYP inhibitory promiscuity	+	0.6853	68.53%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Danger	0.4417	44.17%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.8017	80.17%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7638	76.38%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7707	77.07%
Acute Oral Toxicity (c)	I	0.3397	33.97%
Estrogen receptor binding	+	0.8181	81.81%
Androgen receptor binding	+	0.8336	83.36%
Thyroid receptor binding	+	0.5910	59.10%
Glucocorticoid receptor binding	+	0.8032	80.32%
Aromatase binding	-	0.5423	54.23%
PPAR gamma	+	0.6620	66.20%
Honey bee toxicity	-	0.6146	61.46%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4393	P39900	Matrix metalloproteinase 12	670 nM	IC50	via Super-PRED
CHEMBL321	P14780	Matrix metalloproteinase 9	990 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.13%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.98%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.77%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.56%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.34%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	89.17%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.90%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.78%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.27%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	84.91%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.22%	95.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.52%	95.71%
CHEMBL2535	P11166	Glucose transporter	80.62%	98.75%

Plants that contains it

• Salvia miltiorrhiza

Cross-Links

• PubChem: 163190756
• LOTUS: LTS0249974
• wikiData: Q105345672