3-(3,5-Dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

Details

• Internal ID: 3236f5a3-e9c6-450a-96c2-19d941ae390b
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=O)C4=CC(=CC(=C4)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=O)C4=CC(=CC(=C4)O)O)O
• InChI: InChI=1S/C21H16O5/c22-11-12-1-6-19-18(7-12)20(14-8-16(24)10-17(25)9-14)21(26-19)13-2-4-15(23)5-3-13/h1-11,20-21,23-25H
• InChI Key: TYAYDVXOPBERFS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₅
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.88
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	-	0.7762	77.62%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7074	70.74%
OATP2B1 inhibitior	-	0.5808	58.08%
OATP1B1 inhibitior	+	0.6869	68.69%
OATP1B3 inhibitior	-	0.5072	50.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6042	60.42%
P-glycoprotein inhibitior	-	0.7576	75.76%
P-glycoprotein substrate	-	0.9385	93.85%
CYP3A4 substrate	-	0.5137	51.37%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.6633	66.33%
CYP3A4 inhibition	+	0.6304	63.04%
CYP2C9 inhibition	+	0.8922	89.22%
CYP2C19 inhibition	+	0.8259	82.59%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	+	0.9371	93.71%
CYP2C8 inhibition	+	0.6714	67.14%
CYP inhibitory promiscuity	+	0.8960	89.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5116	51.16%
Eye corrosion	-	0.9919	99.19%
Eye irritation	+	0.8956	89.56%
Skin irritation	+	0.5843	58.43%
Skin corrosion	-	0.9684	96.84%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5361	53.61%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	-	0.5347	53.47%
skin sensitisation	-	0.8117	81.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7683	76.83%
Acute Oral Toxicity (c)	III	0.4986	49.86%
Estrogen receptor binding	+	0.5774	57.74%
Androgen receptor binding	+	0.6904	69.04%
Thyroid receptor binding	+	0.6312	63.12%
Glucocorticoid receptor binding	+	0.7794	77.94%
Aromatase binding	+	0.6785	67.85%
PPAR gamma	+	0.7661	76.61%
Honey bee toxicity	-	0.7993	79.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9709	97.09%

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	97.25%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.63%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.37%	91.49%
CHEMBL3194	P02766	Transthyretin	91.11%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.37%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.36%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.16%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.16%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.55%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.37%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.12%	97.09%

Plants that contains it

• Smilax bracteata

Cross-Links

• PubChem: 22297429
• LOTUS: LTS0056701
• wikiData: Q105267216