(2S,3S)-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-carboxylic acid

Details

• Internal ID: 1135be4d-e1f9-4a7d-9229-956efd851007
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3S)-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-carboxylic acid
• SMILES (Canonical): COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O
• SMILES (Isomeric): COC(=O)[C@@H](CC1=CC(=C(C=C1)O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O
• InChI: InChI=1S/C28H24O12/c1-38-28(37)21(11-13-2-6-16(29)19(32)10-13)39-22(34)9-5-14-3-8-18(31)26-23(14)24(27(35)36)25(40-26)15-4-7-17(30)20(33)12-15/h2-10,12,21,24-25,29-33H,11H2,1H3,(H,35,36)/b9-5+/t21-,24+,25-/m1/s1
• InChI Key: YQEVPWOGQQZUKO-YKMFFSNCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₂
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.12677620 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9345	93.45%
Caco-2	-	0.8987	89.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7305	73.05%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.8830	88.30%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8499	84.99%
P-glycoprotein inhibitior	+	0.7272	72.72%
P-glycoprotein substrate	-	0.5737	57.37%
CYP3A4 substrate	+	0.6602	66.02%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8393	83.93%
CYP3A4 inhibition	-	0.6883	68.83%
CYP2C9 inhibition	+	0.8293	82.93%
CYP2C19 inhibition	+	0.5442	54.42%
CYP2D6 inhibition	-	0.8919	89.19%
CYP1A2 inhibition	-	0.6203	62.03%
CYP2C8 inhibition	+	0.7550	75.50%
CYP inhibitory promiscuity	+	0.6473	64.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Danger	0.4690	46.90%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8728	87.28%
Skin irritation	-	0.7698	76.98%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6920	69.20%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8457	84.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8686	86.86%
Acute Oral Toxicity (c)	III	0.3238	32.38%
Estrogen receptor binding	+	0.8115	81.15%
Androgen receptor binding	+	0.8228	82.28%
Thyroid receptor binding	+	0.5593	55.93%
Glucocorticoid receptor binding	+	0.7480	74.80%
Aromatase binding	-	0.6198	61.98%
PPAR gamma	+	0.6336	63.36%
Honey bee toxicity	-	0.6704	67.04%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9871	98.71%

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	99.50%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.41%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.46%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.28%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.12%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.48%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.06%	95.50%
CHEMBL2581	P07339	Cathepsin D	89.59%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	89.24%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.23%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.02%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.02%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.39%	90.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.99%	95.71%
CHEMBL233	P35372	Mu opioid receptor	81.05%	97.93%
CHEMBL3194	P02766	Transthyretin	80.52%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.46%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	80.01%	94.73%

Plants that contains it

• Lithospermum erythrorhizon

Cross-Links

• PubChem: 25256838
• NPASS: NPC223006
• LOTUS: LTS0230543
• wikiData: Q105352204