Fisetin tetramethyl ether

Details

• Internal ID: b5e4465f-b533-49c5-8d32-c77e5e8f11b6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-3,7-dimethoxychromen-4-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C(=O)C(=C(O2)C3=CC(=C(C=C3)OC)OC)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)C(=O)C(=C(O2)C3=CC(=C(C=C3)OC)OC)OC
• InChI: InChI=1S/C19H18O6/c1-21-12-6-7-13-15(10-12)25-18(19(24-4)17(13)20)11-5-8-14(22-2)16(9-11)23-3/h5-10H,1-4H3
• InChI Key: NAMFTZBUZYVNST-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.30 g/mol
• Exact Mass: 342.11033829 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• Fisetin tetramethyl ether
• 3,3',4',7-Tetramethoxyflavone
• MK6JUA2E4J
• UNII-MK6JUA2E4J
• 3,3',4',7-Tetra-O-methylfisetin
• 17093-86-6
• Flavone, 3,3',4',7-tetramethoxy-
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,7-dimethoxy-
• 2-(3,4-Dimethoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one
• 2-(3,4-Dimethoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
• Tetramethyl fisetine
• CHEMBL575808
• SCHEMBL7116147
• 3,7,3',4'-tetramethoxyflavone
• NAMFTZBUZYVNST-UHFFFAOYSA-N
• BDBM50439844
• LMPK12111571
• 2-(3,4-Dimethoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.9159	91.59%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9710	97.10%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6568	65.68%
P-glycoprotein inhibitior	+	0.9426	94.26%
P-glycoprotein substrate	-	0.7761	77.61%
CYP3A4 substrate	+	0.5552	55.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.6138	61.38%
CYP2C9 inhibition	-	0.7985	79.85%
CYP2C19 inhibition	+	0.7445	74.45%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	+	0.9694	96.94%
CYP2C8 inhibition	+	0.7239	72.39%
CYP inhibitory promiscuity	+	0.8123	81.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5636	56.36%
Eye corrosion	-	0.9682	96.82%
Eye irritation	+	0.6614	66.14%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6491	64.91%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.5225	52.25%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7298	72.98%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.9403	94.03%
Androgen receptor binding	+	0.8957	89.57%
Thyroid receptor binding	+	0.6587	65.87%
Glucocorticoid receptor binding	+	0.8405	84.05%
Aromatase binding	+	0.7365	73.65%
PPAR gamma	+	0.7932	79.32%
Honey bee toxicity	-	0.8795	87.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9192	91.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	1180 nM; 2140 nM	IC50; IC50	PMID: 23851114; PMID: 23851114

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.80%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	93.99%	93.31%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.98%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.53%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.03%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.38%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	90.28%	92.98%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.39%	96.00%
CHEMBL5747	Q92793	CREB-binding protein	87.66%	95.12%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.48%	86.92%
CHEMBL2581	P07339	Cathepsin D	87.19%	98.95%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.66%	85.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.57%	94.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.49%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.38%	99.17%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.24%	95.53%
CHEMBL4393	P39900	Matrix metalloproteinase 12	82.68%	92.22%
CHEMBL4349	Q02083	N-acylsphingosine-amidohydrolase	82.63%	93.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.22%	99.15%
CHEMBL3438	Q05513	Protein kinase C zeta	82.07%	88.48%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.82%	95.50%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.48%	93.65%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.65%	92.38%

Plants that contains it

• Acacia carneorum
• Acacia fasciculifera
• Acacia mearnsii
• Angelica acutiloba
• Artemisia alba subsp. alba
• Cyperus papyrus
• Dimorphotheca tragus
• Fagus grandifolia
• Ichthyothere latifolia
• Mitragyna inermis
• Neorautanenia ficifolia
• Othonna dentata
• Perriera orientalis
• Pongamia pinnata
• Pongamia pinnata var. pinnata
• Pseudofumaria lutea
• Pteris cretica subsp. cretica
• Sabal palmetto
• Scrophularia oblongifolia
• Solanum chenopodioides
• Strychnos erichsonii
• Swertia pseudochinensis
• Umtiza listeriana

Cross-Links

• PubChem: 631171
• NPASS: NPC299923
• ChEMBL: CHEMBL575808
• LOTUS: LTS0198121
• wikiData: Q105273068