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

Details

• Internal ID: bbfb6e01-a6ae-4336-a26e-c73571fde607
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: 2-[(3,4-dihydroxyphenyl)methylidene]-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): COC1=C(C=CC2=C1OC(=CC3=CC(=C(C=C3)O)O)C2=O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC2=C1OC(=CC3=CC(=C(C=C3)O)O)C2=O)OC4C(C(C(C(O4)CO)O)O)O
• InChI: InChI=1S/C22H22O11/c1-30-21-13(32-22-19(29)18(28)17(27)15(8-23)33-22)5-3-10-16(26)14(31-20(10)21)7-9-2-4-11(24)12(25)6-9/h2-7,15,17-19,22-25,27-29H,8H2,1H3
• InChI Key: NXOKVARAWXQHGX-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.10
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• DTXSID501318728
• 486-23-7
• LMPK12130015

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7757	77.57%
Caco-2	-	0.9084	90.84%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6539	65.39%
OATP2B1 inhibitior	-	0.6991	69.91%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9782	97.82%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7104	71.04%
P-glycoprotein inhibitior	-	0.6478	64.78%
P-glycoprotein substrate	-	0.8169	81.69%
CYP3A4 substrate	+	0.6029	60.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.8150	81.50%
CYP2C9 inhibition	-	0.8010	80.10%
CYP2C19 inhibition	-	0.6606	66.06%
CYP2D6 inhibition	-	0.8373	83.73%
CYP1A2 inhibition	-	0.8042	80.42%
CYP2C8 inhibition	+	0.5570	55.70%
CYP inhibitory promiscuity	+	0.6133	61.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5732	57.32%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8926	89.26%
Skin irritation	-	0.7951	79.51%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8154	81.54%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7559	75.59%
Acute Oral Toxicity (c)	III	0.6053	60.53%
Estrogen receptor binding	+	0.7771	77.71%
Androgen receptor binding	+	0.6528	65.28%
Thyroid receptor binding	+	0.5733	57.33%
Glucocorticoid receptor binding	+	0.6229	62.29%
Aromatase binding	-	0.6075	60.75%
PPAR gamma	+	0.7400	74.00%
Honey bee toxicity	-	0.7355	73.55%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8947	89.47%

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	99.87%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.25%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.75%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.44%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.52%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.53%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	90.14%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.52%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.55%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.47%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.42%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.15%	80.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.39%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.86%	83.82%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.16%	95.53%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.92%	96.90%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.52%	99.23%

Plants that contains it

• Coreopsis grandiflora
• Coreopsis lanceolata
• Vaccinium oxycoccos

Cross-Links

• PubChem: 42607750
• LOTUS: LTS0167755
• wikiData: Q105384704