5,7-Dihydroxy-4-[2-(4-hydroxyphenyl)ethenyl]chromen-2-one

Details

• Internal ID: 5110006f-a58e-4d83-803a-c4c4dfb0ab3d
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 5,7-dihydroxy-4-[2-(4-hydroxyphenyl)ethenyl]chromen-2-one
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=CC(=O)OC3=CC(=CC(=C23)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C=CC2=CC(=O)OC3=CC(=CC(=C23)O)O)O
• InChI: InChI=1S/C17H12O5/c18-12-5-2-10(3-6-12)1-4-11-7-16(21)22-15-9-13(19)8-14(20)17(11)15/h1-9,18-20H
• InChI Key: QZYJYWPBQCRMEZ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₅
• Molecular Weight: 296.27 g/mol
• Exact Mass: 296.06847348 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9581	95.81%
Caco-2	+	0.8263	82.63%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4461	44.61%
OATP2B1 inhibitior	-	0.6866	68.66%
OATP1B1 inhibitior	+	0.8093	80.93%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4833	48.33%
P-glycoprotein inhibitior	-	0.8104	81.04%
P-glycoprotein substrate	-	0.9227	92.27%
CYP3A4 substrate	-	0.5289	52.89%
CYP2C9 substrate	-	0.6057	60.57%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	+	0.8690	86.90%
CYP2C9 inhibition	-	0.6821	68.21%
CYP2C19 inhibition	-	0.7179	71.79%
CYP2D6 inhibition	-	0.9440	94.40%
CYP1A2 inhibition	-	0.5096	50.96%
CYP2C8 inhibition	+	0.6651	66.51%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9794	97.94%
Eye irritation	+	0.9405	94.05%
Skin irritation	+	0.5994	59.94%
Skin corrosion	-	0.9786	97.86%
Ames mutagenesis	+	0.5246	52.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.8404	84.04%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.6165	61.65%
skin sensitisation	-	0.7450	74.50%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5081	50.81%
Estrogen receptor binding	+	0.9482	94.82%
Androgen receptor binding	+	0.9327	93.27%
Thyroid receptor binding	+	0.6304	63.04%
Glucocorticoid receptor binding	+	0.9459	94.59%
Aromatase binding	+	0.9285	92.85%
PPAR gamma	+	0.9343	93.43%
Honey bee toxicity	-	0.8195	81.95%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9457	94.57%

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	98.94%	91.11%
CHEMBL3194	P02766	Transthyretin	98.64%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	93.60%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.52%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.47%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	90.73%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.57%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.88%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.62%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.15%	96.00%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL3959	P16083	Quinone reductase 2	83.69%	89.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.37%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	81.75%	91.49%

Plants that contains it

• Ononis vaginalis

Cross-Links

• PubChem: 85108003
• LOTUS: LTS0272031
• wikiData: Q105232454