(2Z)-2-benzylidene-4,5,6-trihydroxy-1-benzofuran-3-one

Details

• Internal ID: e8ce6e03-f67b-4498-b5bb-e771336d1b2c
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids
• IUPAC Name: (2Z)-2-benzylidene-4,5,6-trihydroxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC=C(C=C1)C=C2C(=O)C3=C(O2)C=C(C(=C3O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)/C=C\2/C(=O)C3=C(O2)C=C(C(=C3O)O)O
• InChI: InChI=1S/C15H10O5/c16-9-7-10-12(15(19)13(9)17)14(18)11(20-10)6-8-4-2-1-3-5-8/h1-7,16-17,19H/b11-6-
• InChI Key: DYDUQRQYDQHKJU-WDZFZDKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24 g/mol
• Exact Mass: 270.05282342 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9831	98.31%
Caco-2	-	0.9226	92.26%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5189	51.89%
OATP2B1 inhibitior	-	0.7112	71.12%
OATP1B1 inhibitior	+	0.8841	88.41%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8403	84.03%
P-glycoprotein inhibitior	-	0.8308	83.08%
P-glycoprotein substrate	-	0.9853	98.53%
CYP3A4 substrate	-	0.6395	63.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8409	84.09%
CYP3A4 inhibition	+	0.5482	54.82%
CYP2C9 inhibition	-	0.6091	60.91%
CYP2C19 inhibition	-	0.7345	73.45%
CYP2D6 inhibition	-	0.8858	88.58%
CYP1A2 inhibition	+	0.9402	94.02%
CYP2C8 inhibition	-	0.6003	60.03%
CYP inhibitory promiscuity	+	0.8920	89.20%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4353	43.53%
Eye corrosion	-	0.9859	98.59%
Eye irritation	+	0.9650	96.50%
Skin irritation	+	0.5420	54.20%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8710	87.10%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	+	0.5529	55.29%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6937	69.37%
Acute Oral Toxicity (c)	IV	0.3730	37.30%
Estrogen receptor binding	+	0.6966	69.66%
Androgen receptor binding	+	0.8498	84.98%
Thyroid receptor binding	+	0.6773	67.73%
Glucocorticoid receptor binding	+	0.8058	80.58%
Aromatase binding	+	0.7304	73.04%
PPAR gamma	+	0.7416	74.16%
Honey bee toxicity	-	0.9034	90.34%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9874	98.74%

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	99.25%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.26%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.94%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.62%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.40%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.54%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.34%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.10%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.42%	94.62%
CHEMBL3194	P02766	Transthyretin	84.43%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.86%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.33%	96.00%

Plants that contains it

• Boschniakia rossica
• Scutellaria baicalensis

Cross-Links

• PubChem: 5322048
• NPASS: NPC149487