Eupatolin

Details

• Internal ID: 627a910a-e2eb-4e10-bd2b-7473447b9d68
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=C(C(=C3C2=O)O)OC)OC)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=C(C(=C3C2=O)O)OC)OC)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C23H24O12/c1-8-15(26)18(29)19(30)23(33-8)35-22-17(28)14-12(7-13(31-2)21(32-3)16(14)27)34-20(22)9-4-5-10(24)11(25)6-9/h4-8,15,18-19,23-27,29-30H,1-3H3/t8-,15-,18+,19+,23-/m0/s1
• InChI Key: NVZCGVLCUJLTSA-BOCAMIPNSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₂
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.12677620 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• RE3LW4CY9C
• eupatolitin 3-O-rhamnoside
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 29725-50-6
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-
• 4H-1-Benzopyran-4-one, 3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-
• UNII-RE3LW4CY9C
• CHEMBL4635075
• CHEBI:192422
• HY-N10988
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CS-0638112
• Eupatolitin, 3-(6-deoxy-alpha-L-mannopyranoside)
• Q5409926
• EUPATOLITIN, 3-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSIDE)
• 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6,7-DIMETHOXY-4H-1-BENZOPYRAN-4-ONE
• 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7908	79.08%
Caco-2	-	0.7979	79.79%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6385	63.85%
OATP2B1 inhibitior	-	0.5559	55.59%
OATP1B1 inhibitior	+	0.9419	94.19%
OATP1B3 inhibitior	+	0.8712	87.12%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6174	61.74%
P-glycoprotein inhibitior	+	0.5719	57.19%
P-glycoprotein substrate	-	0.5642	56.42%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	-	0.7502	75.02%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.7793	77.93%
CYP2C9 inhibition	-	0.9748	97.48%
CYP2C19 inhibition	-	0.9206	92.06%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.7894	78.94%
CYP2C8 inhibition	+	0.8575	85.75%
CYP inhibitory promiscuity	-	0.6067	60.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5397	53.97%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.8180	81.80%
Skin irritation	-	0.7365	73.65%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5201	52.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.6030	60.30%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9317	93.17%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9473	94.73%
Acute Oral Toxicity (c)	II	0.4554	45.54%
Estrogen receptor binding	+	0.7588	75.88%
Androgen receptor binding	+	0.6420	64.20%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.5297	52.97%
PPAR gamma	+	0.6533	65.33%
Honey bee toxicity	-	0.7602	76.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.9209	92.09%

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	99.54%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.73%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.68%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.58%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.01%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	94.70%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.80%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.49%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.42%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.65%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.12%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.69%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	86.47%	94.73%
CHEMBL3194	P02766	Transthyretin	83.24%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.13%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.97%	99.23%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.20%	94.03%

Plants that contains it

• Ageratina ligustrina
• Anthemis anthemiformis
• Brickellia secundiflora
• Brickellia vernicosa
• Citrus aurantiifolia
• Eupatorium fortunei
• Lysimachia clethroides
• Rudbeckia mollis
• Senna sophera
• Stevia vaga

Cross-Links

• PubChem: 5317290
• NPASS: NPC27640
• LOTUS: LTS0110886
• wikiData: Q5409926