Fisetin 3-methyl ether

Details

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Internal ID ee8a4b57-0986-4270-9f4b-775827c24d8b
Taxonomy Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
IUPAC Name 2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxychromen-4-one
SMILES (Canonical) COC1=C(OC2=C(C1=O)C=CC(=C2)O)C3=CC(=C(C=C3)O)O
SMILES (Isomeric) COC1=C(OC2=C(C1=O)C=CC(=C2)O)C3=CC(=C(C=C3)O)O
InChI InChI=1S/C16H12O6/c1-21-16-14(20)10-4-3-9(17)7-13(10)22-15(16)8-2-5-11(18)12(19)6-8/h2-7,17-19H,1H3
InChI Key VBXMLZNGZPQAEI-UHFFFAOYSA-N
Popularity 10 references in papers

Physical and Chemical Properties

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Molecular Formula C16H12O6
Molecular Weight 300.26 g/mol
Exact Mass 300.06338810 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.59
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxychromen-4-one
3-O-Methylfisetin
SCHEMBL34716
CHEMBL126121
CHEBI:184653
LMPK12111567
7,3',4'-trihydroxy-3-methoxyflavone

2D Structure

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2D Structure of Fisetin 3-methyl ether

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9577 95.77%
Caco-2 - 0.6113 61.13%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.7944 79.44%
OATP2B1 inhibitior + 0.5620 56.20%
OATP1B1 inhibitior + 0.9562 95.62%
OATP1B3 inhibitior + 0.9965 99.65%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.6383 63.83%
P-glycoprotein inhibitior - 0.7550 75.50%
P-glycoprotein substrate - 0.7484 74.84%
CYP3A4 substrate + 0.5477 54.77%
CYP2C9 substrate - 0.8397 83.97%
CYP2D6 substrate - 0.7876 78.76%
CYP3A4 inhibition - 0.7179 71.79%
CYP2C9 inhibition + 0.5494 54.94%
CYP2C19 inhibition + 0.6827 68.27%
CYP2D6 inhibition - 0.9018 90.18%
CYP1A2 inhibition + 0.9263 92.63%
CYP2C8 inhibition + 0.8694 86.94%
CYP inhibitory promiscuity + 0.6056 60.56%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5596 55.96%
Eye corrosion - 0.9766 97.66%
Eye irritation + 0.7362 73.62%
Skin irritation - 0.5899 58.99%
Skin corrosion - 0.9443 94.43%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8641 86.41%
Micronuclear + 0.9100 91.00%
Hepatotoxicity + 0.7447 74.47%
skin sensitisation - 0.9318 93.18%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.7774 77.74%
Acute Oral Toxicity (c) III 0.6733 67.33%
Estrogen receptor binding + 0.8900 89.00%
Androgen receptor binding + 0.9240 92.40%
Thyroid receptor binding + 0.5282 52.82%
Glucocorticoid receptor binding + 0.8545 85.45%
Aromatase binding + 0.8473 84.73%
PPAR gamma + 0.7085 70.85%
Honey bee toxicity - 0.8698 86.98%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8838 88.38%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.43% 91.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 94.52% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.92% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.81% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 93.22% 94.00%
CHEMBL2581 P07339 Cathepsin D 93.00% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.48% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.11% 86.33%
CHEMBL242 Q92731 Estrogen receptor beta 90.81% 98.35%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 89.61% 80.78%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.04% 85.14%
CHEMBL1951 P21397 Monoamine oxidase A 86.37% 91.49%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.09% 99.17%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 84.65% 95.53%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.45% 99.23%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 82.84% 93.65%
CHEMBL1907 P15144 Aminopeptidase N 82.56% 93.31%
CHEMBL3401 O75469 Pregnane X receptor 82.51% 94.73%
CHEMBL3194 P02766 Transthyretin 81.97% 90.71%
CHEMBL2535 P11166 Glucose transporter 81.64% 98.75%
CHEMBL1163101 O75460 Serine/threonine-protein kinase/endoribonuclease IRE1 80.84% 98.11%

Cross-Links

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PubChem 9839293
NPASS NPC260895
ChEMBL CHEMBL126121
LOTUS LTS0066001
wikiData Q105283550