Eupatolitin

Details

• Internal ID: 083d69e3-17c5-44e4-9b43-684a31f8d362
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)O)O)OC
• InChI: InChI=1S/C17H14O8/c1-23-11-6-10-12(14(21)17(11)24-2)13(20)15(22)16(25-10)7-3-4-8(18)9(19)5-7/h3-6,18-19,21-22H,1-2H3
• InChI Key: WYKWHSPRHPZRCR-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₈
• Molecular Weight: 346.30 g/mol
• Exact Mass: 346.06886740 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• Eupatoletin
• 29536-44-5
• 9KB4QHZ4YG
• 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxychromen-4-one
• 3,3',4',5-tetrahydroxy-6,7-dimethoxyflavone
• 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxy-
• UNII-9KB4QHZ4YG
• 6-Methoxy-7-methylquercetin
• CHEBI:81340
• DTXSID80183724
• HY-N10886
• LMPK12112994
• AKOS040735123
• CS-0637328
• 3,5,3',4'-tetrahydroxy-6,7-dimethoxyflavone
• C17788
• Q5409931
• FLAVONE, 3,3',4',5-TETRAHYDROXY-6,7-DIMETHOXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9497	94.97%
Caco-2	+	0.6426	64.26%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7985	79.85%
OATP2B1 inhibitior	-	0.5431	54.31%
OATP1B1 inhibitior	+	0.9605	96.05%
OATP1B3 inhibitior	+	0.9910	99.10%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6565	65.65%
P-glycoprotein inhibitior	-	0.5741	57.41%
P-glycoprotein substrate	-	0.7733	77.33%
CYP3A4 substrate	+	0.5706	57.06%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.6426	64.26%
CYP2C9 inhibition	-	0.6061	60.61%
CYP2C19 inhibition	+	0.6079	60.79%
CYP2D6 inhibition	-	0.8565	85.65%
CYP1A2 inhibition	+	0.8621	86.21%
CYP2C8 inhibition	+	0.9351	93.51%
CYP inhibitory promiscuity	+	0.5928	59.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6148	61.48%
Eye corrosion	-	0.9795	97.95%
Eye irritation	+	0.5833	58.33%
Skin irritation	-	0.6593	65.93%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	+	0.5336	53.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.6813	68.13%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9292	92.92%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9095	90.95%
Acute Oral Toxicity (c)	III	0.5027	50.27%
Estrogen receptor binding	+	0.8399	83.99%
Androgen receptor binding	+	0.7752	77.52%
Thyroid receptor binding	+	0.6020	60.20%
Glucocorticoid receptor binding	+	0.8200	82.00%
Aromatase binding	+	0.6605	66.05%
PPAR gamma	+	0.8368	83.68%
Honey bee toxicity	-	0.8360	83.60%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.9062	90.62%

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	99.02%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.84%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.16%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.19%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.77%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.34%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.36%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.20%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.98%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.30%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.96%	80.78%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	85.96%	98.11%
CHEMBL3194	P02766	Transthyretin	85.92%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.97%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.95%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.05%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.99%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.47%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	81.10%	91.49%

Plants that contains it

• Ageratina areolaris
• Ageratina ligustrina
• Artemisia annua
• Artemisia capillaris
• Bishopanthus soliceps
• Brickellia dentata
• Brickellia glutinosa
• Brickellia veronicaefolia
• Dicoma tomentosa
• Eupatorium fortunei
• Haplopappus foliosus
• Ipomopsis aggregata
• Ipomopsis polycladon
• Rudbeckia hirta var. pulcherrima

Cross-Links

• PubChem: 5317291
• NPASS: NPC287462
• LOTUS: LTS0100502
• wikiData: Q5409931