(E)-4-(3,4-Dihydroxystyryl)-2-oxo-2H-pyran-6-carboxylic acid

Details

• Internal ID: 215fb409-6632-44a6-ae37-4742f80f8f1d
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-6-oxopyran-2-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=O)OC(=C2)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C2=CC(=O)OC(=C2)C(=O)O)O)O
• InChI: InChI=1S/C14H10O6/c15-10-4-3-8(5-11(10)16)1-2-9-6-12(14(18)19)20-13(17)7-9/h1-7,15-16H,(H,18,19)/b2-1+
• InChI Key: ZUIOVKAJONGJHT-OWOJBTEDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.22 g/mol
• Exact Mass: 274.04773803 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• (E)-4-(3,4-Dihydroxystyryl)-2-oxo-2H-pyran-6-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8447	84.47%
Caco-2	-	0.7579	75.79%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7555	75.55%
OATP2B1 inhibitior	-	0.7023	70.23%
OATP1B1 inhibitior	+	0.9632	96.32%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6613	66.13%
P-glycoprotein inhibitior	-	0.9583	95.83%
P-glycoprotein substrate	-	0.9793	97.93%
CYP3A4 substrate	-	0.6681	66.81%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8871	88.71%
CYP3A4 inhibition	-	0.8392	83.92%
CYP2C9 inhibition	+	0.5064	50.64%
CYP2C19 inhibition	-	0.8141	81.41%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.9367	93.67%
CYP2C8 inhibition	-	0.8120	81.20%
CYP inhibitory promiscuity	-	0.8250	82.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6403	64.03%
Eye corrosion	-	0.9833	98.33%
Eye irritation	+	0.7299	72.99%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9024	90.24%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8810	88.10%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5101	51.01%
skin sensitisation	-	0.6138	61.38%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6679	66.79%
Acute Oral Toxicity (c)	III	0.4593	45.93%
Estrogen receptor binding	+	0.7764	77.64%
Androgen receptor binding	+	0.8666	86.66%
Thyroid receptor binding	-	0.5918	59.18%
Glucocorticoid receptor binding	+	0.8440	84.40%
Aromatase binding	+	0.8187	81.87%
PPAR gamma	+	0.7886	78.86%
Honey bee toxicity	-	0.8363	83.63%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	98.44%	91.11%
CHEMBL3194	P02766	Transthyretin	96.52%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.14%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.72%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.67%	96.00%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.18%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	85.07%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.91%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.80%	90.71%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	81.57%	83.65%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.25%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.66%	94.45%

Plants that contains it

• Dumortiera hirsuta

Cross-Links

• PubChem: 101995378
• LOTUS: LTS0118719
• wikiData: Q105383693