2-[(3,4-Dihydroxyphenyl)methylidene]-4,6-dihydroxy-5-methyl-1-benzofuran-3-one

Details

• Internal ID: 5ee26c05-f747-4d64-acdd-c37a9dd5de81
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids
• IUPAC Name: 2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-5-methyl-1-benzofuran-3-one
• SMILES (Canonical): CC1=C(C2=C(C=C1O)OC(=CC3=CC(=C(C=C3)O)O)C2=O)O
• SMILES (Isomeric): CC1=C(C2=C(C=C1O)OC(=CC3=CC(=C(C=C3)O)O)C2=O)O
• InChI: InChI=1S/C16H12O6/c1-7-10(18)6-12-14(15(7)20)16(21)13(22-12)5-8-2-3-9(17)11(19)4-8/h2-6,17-20H,1H3
• InChI Key: LEAOMQYNYFRDAT-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.5462	54.62%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5989	59.89%
OATP2B1 inhibitior	+	0.5638	56.38%
OATP1B1 inhibitior	+	0.9003	90.03%
OATP1B3 inhibitior	+	0.9802	98.02%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6632	66.32%
P-glycoprotein inhibitior	-	0.8803	88.03%
P-glycoprotein substrate	-	0.9651	96.51%
CYP3A4 substrate	-	0.5502	55.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.5154	51.54%
CYP2C9 inhibition	+	0.5366	53.66%
CYP2C19 inhibition	-	0.6147	61.47%
CYP2D6 inhibition	-	0.8888	88.88%
CYP1A2 inhibition	+	0.9670	96.70%
CYP2C8 inhibition	-	0.6883	68.83%
CYP inhibitory promiscuity	+	0.9209	92.09%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.3881	38.81%
Eye corrosion	-	0.9865	98.65%
Eye irritation	+	0.8697	86.97%
Skin irritation	-	0.5265	52.65%
Skin corrosion	-	0.8795	87.95%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8151	81.51%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7108	71.08%
Acute Oral Toxicity (c)	III	0.3763	37.63%
Estrogen receptor binding	+	0.8582	85.82%
Androgen receptor binding	+	0.8671	86.71%
Thyroid receptor binding	+	0.6292	62.92%
Glucocorticoid receptor binding	+	0.7830	78.30%
Aromatase binding	+	0.6553	65.53%
PPAR gamma	+	0.8215	82.15%
Honey bee toxicity	-	0.8765	87.65%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.76%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.34%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.17%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.19%	94.73%
CHEMBL2581	P07339	Cathepsin D	91.65%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.05%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.68%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.80%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.63%	94.45%
CHEMBL3194	P02766	Transthyretin	85.34%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.22%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.52%	93.40%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.44%	96.12%

Plants that contains it

• Cyperus capitatus

Cross-Links

• PubChem: 74819317
• LOTUS: LTS0251376
• wikiData: Q105150481