2-[(3,4-Dihydroxyphenyl)methylidene]-6-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one

Details

• Internal ID: d98f320f-523e-4008-9dd8-9b679580060d
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids
• IUPAC Name: 2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=C(C=C1C=C2C(=O)C3=C(O2)C(=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C=C2C(=O)C3=C(O2)C(=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-14-16(27)17(28)18(29)21(31-14)32-20-11(24)4-2-9-15(26)13(30-19(9)20)6-8-1-3-10(23)12(25)5-8/h1-6,14,16-18,21-25,27-29H,7H2
• InChI Key: WDGSPYHJXBEAQC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7573	75.73%
Caco-2	-	0.9354	93.54%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6583	65.83%
OATP2B1 inhibitior	+	0.5818	58.18%
OATP1B1 inhibitior	+	0.8921	89.21%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6125	61.25%
P-glycoprotein inhibitior	-	0.6764	67.64%
P-glycoprotein substrate	-	0.9106	91.06%
CYP3A4 substrate	+	0.5653	56.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.8343	83.43%
CYP2C9 inhibition	-	0.8566	85.66%
CYP2C19 inhibition	-	0.7065	70.65%
CYP2D6 inhibition	-	0.8217	82.17%
CYP1A2 inhibition	-	0.7979	79.79%
CYP2C8 inhibition	+	0.4639	46.39%
CYP inhibitory promiscuity	+	0.5372	53.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6352	63.52%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8332	83.32%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5867	58.67%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7861	78.61%
Acute Oral Toxicity (c)	III	0.4589	45.89%
Estrogen receptor binding	+	0.6207	62.07%
Androgen receptor binding	+	0.6890	68.90%
Thyroid receptor binding	+	0.5693	56.93%
Glucocorticoid receptor binding	-	0.4696	46.96%
Aromatase binding	-	0.5475	54.75%
PPAR gamma	+	0.6719	67.19%
Honey bee toxicity	-	0.6642	66.42%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9415	94.15%

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	99.86%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.60%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.53%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.79%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.11%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.09%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.00%	95.83%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.36%	80.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.78%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.26%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.45%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.15%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.58%	96.09%
CHEMBL3194	P02766	Transthyretin	81.28%	90.71%

Plants that contains it

• Bidens pilosa

Cross-Links

• PubChem: 74819305
• LOTUS: LTS0160869
• wikiData: Q105016527