Eupafolin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	e7029c44-f98a-43d0-9195-79b42dea0d13
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 6-O-methylated flavonoids
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
SMILES (Canonical)	COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
SMILES (Isomeric)	COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O
InChI	InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
InChI Key	FHHSEFRSDKWJKJ-UHFFFAOYSA-N
Popularity	200 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₆H₁₂O₇
Molecular Weight	316.26 g/mol
Exact Mass	316.05830272 g/mol
Topological Polar Surface Area (TPSA)	116.00 Å²
XlogP	1.40
Atomic LogP (AlogP)	2.29
H-Bond Acceptor	7
H-Bond Donor	4
Rotatable Bonds	2

Synonyms

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Nepetin

520-11-6

EUPAFOLIN

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

Eurafolin

UNII-I3O7LF3GED

I3O7LF3GED

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-

Flavone, 3',4',5,7-tetrahydroxy-6-methoxy-

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	+	0.7570	75.70%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6297	62.97%
OATP2B1 inhibitior	-	0.5435	54.35%
OATP1B1 inhibitior	+	0.9456	94.56%
OATP1B3 inhibitior	+	0.9904	99.04%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7160	71.60%
P-glycoprotein inhibitior	-	0.7309	73.09%
P-glycoprotein substrate	-	0.9155	91.55%
CYP3A4 substrate	+	0.5166	51.66%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	+	0.6330	63.30%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.6361	63.61%
CYP2D6 inhibition	-	0.8687	86.87%
CYP1A2 inhibition	+	0.9091	90.91%
CYP2C8 inhibition	+	0.7042	70.42%
CYP inhibitory promiscuity	+	0.7089	70.89%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6208	62.08%
Eye corrosion	-	0.9790	97.90%
Eye irritation	+	0.8503	85.03%
Skin irritation	-	0.6006	60.06%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7798	77.98%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8781	87.81%
Acute Oral Toxicity (c)	III	0.6309	63.09%
Estrogen receptor binding	+	0.8874	88.74%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6766	67.66%
Glucocorticoid receptor binding	+	0.8584	85.84%
Aromatase binding	+	0.6529	65.29%
PPAR gamma	+	0.8171	81.71%
Honey bee toxicity	-	0.8045	80.45%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8562	85.62%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	11220.2 nM 8912.5 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	44668.4 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	6309.6 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	6309.6 nM	Potency	via CMAUP
CHEMBL1741189	P55789	FAD-linked sulfhydryl oxidase ALR	230 nM	AC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	10000 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5623.4 nM	Potency	via CMAUP
CHEMBL2478	P04745	Salivary alpha-amylase	48000 nM	IC50	PMID: 18507367

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.00%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.90%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.89%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.65%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.47%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.72%	94.45%
CHEMBL3194	P02766	Transthyretin	88.83%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	87.61%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.20%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.40%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	83.20%	94.73%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	81.90%	98.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.20%	90.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.