4-[3-[1-Carboxy-2-(4-hydroxy-3-methoxyphenyl)ethoxy]-3-oxoprop-1-enyl]-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid

Details

• Internal ID: 307474fb-29fd-4fae-be68-99a5d8004ea9
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[3-[1-carboxy-2-(4-hydroxy-3-methoxyphenyl)ethoxy]-3-oxoprop-1-enyl]-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)CC(C(=O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)OC)C(=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC(C(=O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)OC)C(=O)O)O
• InChI: InChI=1S/C29H26O12/c1-38-20-11-14(3-7-17(20)30)12-22(28(34)35)40-23(33)10-6-15-4-9-19(32)27-24(15)25(29(36)37)26(41-27)16-5-8-18(31)21(13-16)39-2/h3-11,13,22,25-26,30-32H,12H2,1-2H3,(H,34,35)(H,36,37)
• InChI Key: QQPFHBFQFCFWRM-UHFFFAOYSA-N
• Popularity: 0 references 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): 3.37
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	-	0.8676	86.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7488	74.88%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.8444	84.44%
OATP1B3 inhibitior	-	0.2243	22.43%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8761	87.61%
P-glycoprotein inhibitior	+	0.8106	81.06%
P-glycoprotein substrate	-	0.5800	58.00%
CYP3A4 substrate	+	0.6532	65.32%
CYP2C9 substrate	-	0.8003	80.03%
CYP2D6 substrate	-	0.8365	83.65%
CYP3A4 inhibition	-	0.7094	70.94%
CYP2C9 inhibition	+	0.7811	78.11%
CYP2C19 inhibition	+	0.5437	54.37%
CYP2D6 inhibition	-	0.8744	87.44%
CYP1A2 inhibition	-	0.6934	69.34%
CYP2C8 inhibition	+	0.8219	82.19%
CYP inhibitory promiscuity	+	0.6643	66.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Danger	0.4504	45.04%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.8144	81.44%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6443	64.43%
Micronuclear	+	0.8777	87.77%
Hepatotoxicity	-	0.7714	77.14%
skin sensitisation	-	0.8331	83.31%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9259	92.59%
Acute Oral Toxicity (c)	III	0.3803	38.03%
Estrogen receptor binding	+	0.8075	80.75%
Androgen receptor binding	+	0.7435	74.35%
Thyroid receptor binding	+	0.6133	61.33%
Glucocorticoid receptor binding	+	0.7727	77.27%
Aromatase binding	-	0.6237	62.37%
PPAR gamma	+	0.6361	63.61%
Honey bee toxicity	-	0.7319	73.19%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9876	98.76%

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	99.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.52%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.66%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.25%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.04%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	93.58%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.29%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.87%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.60%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.06%	95.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.94%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.82%	89.00%
CHEMBL2535	P11166	Glucose transporter	86.25%	98.75%
CHEMBL3194	P02766	Transthyretin	85.03%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.89%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.53%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.35%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.26%	91.19%
CHEMBL1255126	O15151	Protein Mdm4	80.64%	90.20%

Plants that contains it

• Clinopodium chinense

Cross-Links

• PubChem: 74975951
• LOTUS: LTS0035160
• wikiData: Q105225965