5,6-Dihydroxy-7,8-dimethoxy-2-(2-phenylethenyl)pyrano[2,3-b][1]benzofuran-4-one

Details

• Internal ID: 242c0e40-e8bb-40b3-befb-b3fcf38047d6
• Taxonomy: Organoheterocyclic compounds > Furopyrans
• IUPAC Name: 5,6-dihydroxy-7,8-dimethoxy-2-(2-phenylethenyl)pyrano[2,3-b][1]benzofuran-4-one
• SMILES (Canonical): COC1=C(C(=C2C3=C(OC(=CC3=O)C=CC4=CC=CC=C4)OC2=C1OC)O)O
• SMILES (Isomeric): COC1=C(C(=C2C3=C(OC(=CC3=O)C=CC4=CC=CC=C4)OC2=C1OC)O)O
• InChI: InChI=1S/C21H16O7/c1-25-19-17(24)16(23)15-14-13(22)10-12(9-8-11-6-4-3-5-7-11)27-21(14)28-18(15)20(19)26-2/h3-10,23-24H,1-2H3
• InChI Key: QXEBIXCIMOCZGN-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₇
• Molecular Weight: 380.30 g/mol
• Exact Mass: 380.08960285 g/mol
• Topological Polar Surface Area (TPSA): 98.40 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.14
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9483	94.83%
Caco-2	-	0.6352	63.52%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7170	71.70%
OATP2B1 inhibitior	-	0.7156	71.56%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7250	72.50%
P-glycoprotein inhibitior	+	0.8260	82.60%
P-glycoprotein substrate	-	0.8208	82.08%
CYP3A4 substrate	+	0.5098	50.98%
CYP2C9 substrate	-	0.8156	81.56%
CYP2D6 substrate	-	0.8222	82.22%
CYP3A4 inhibition	+	0.5764	57.64%
CYP2C9 inhibition	-	0.7155	71.55%
CYP2C19 inhibition	+	0.8079	80.79%
CYP2D6 inhibition	-	0.5440	54.40%
CYP1A2 inhibition	+	0.5093	50.93%
CYP2C8 inhibition	+	0.7609	76.09%
CYP inhibitory promiscuity	+	0.6655	66.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.5802	58.02%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.6685	66.85%
Skin irritation	-	0.6928	69.28%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4564	45.64%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7612	76.12%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8920	89.20%
Acute Oral Toxicity (c)	II	0.5773	57.73%
Estrogen receptor binding	+	0.9126	91.26%
Androgen receptor binding	+	0.8595	85.95%
Thyroid receptor binding	+	0.6483	64.83%
Glucocorticoid receptor binding	+	0.8902	89.02%
Aromatase binding	+	0.6624	66.24%
PPAR gamma	+	0.9001	90.01%
Honey bee toxicity	-	0.8559	85.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9739	97.39%

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	99.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.81%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.12%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.17%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.03%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	88.88%	94.73%
CHEMBL3194	P02766	Transthyretin	86.88%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.57%	89.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.43%	94.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.64%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.07%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.65%	94.45%

Plants that contains it

• Didymocarpus albicalyx

Cross-Links

• PubChem: 85225431
• LOTUS: LTS0233821
• wikiData: Q105229552