Leucanthogenin

Details

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Internal ID d262cad1-7c27-491d-97bd-f2ba9b8fab69
Taxonomy Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
IUPAC Name 2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-6,7-dimethoxychromen-4-one
SMILES (Canonical) COC1=C(C(=C2C(=C1O)C(=O)C=C(O2)C3=CC(=C(C=C3)O)O)O)OC
SMILES (Isomeric) COC1=C(C(=C2C(=C1O)C(=O)C=C(O2)C3=CC(=C(C=C3)O)O)O)OC
InChI InChI=1S/C17H14O8/c1-23-16-13(21)12-10(20)6-11(7-3-4-8(18)9(19)5-7)25-15(12)14(22)17(16)24-2/h3-6,18-19,21-22H,1-2H3
InChI Key VZNIMRVJHRTTKA-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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

Synonyms

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99615-00-6
5,8,3',4'-Tetrahydroxy-6,7-dimethoxyflavone
8-hydroxycirsiliol
LMPK12111483
AKOS040733987

2D Structure

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2D Structure of Leucanthogenin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9497 94.97%
Caco-2 + 0.5458 54.58%
Blood Brain Barrier - 0.8250 82.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7985 79.85%
OATP2B1 inhibitior - 0.5573 55.73%
OATP1B1 inhibitior + 0.9376 93.76%
OATP1B3 inhibitior + 0.9910 99.10%
MATE1 inhibitior + 0.5400 54.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.7322 73.22%
P-glycoprotein inhibitior - 0.5559 55.59%
P-glycoprotein substrate - 0.9183 91.83%
CYP3A4 substrate + 0.5000 50.00%
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 + 0.6760 67.60%
CYP inhibitory promiscuity + 0.5928 59.28%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6148 61.48%
Eye corrosion - 0.9795 97.95%
Eye irritation + 0.6552 65.52%
Skin irritation - 0.6593 65.93%
Skin corrosion - 0.9509 95.09%
Ames mutagenesis + 0.5036 50.36%
Human Ether-a-go-go-Related Gene inhibition - 0.7777 77.77%
Micronuclear + 0.9100 91.00%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.9292 92.92%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity - 0.8270 82.70%
Acute Oral Toxicity (c) III 0.5027 50.27%
Estrogen receptor binding + 0.8458 84.58%
Androgen receptor binding + 0.8018 80.18%
Thyroid receptor binding + 0.5721 57.21%
Glucocorticoid receptor binding + 0.8223 82.23%
Aromatase binding + 0.6019 60.19%
PPAR gamma + 0.7976 79.76%
Honey bee toxicity - 0.8144 81.44%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9062 90.62%

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 99.45% 91.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.31% 99.15%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.26% 94.00%
CHEMBL2581 P07339 Cathepsin D 94.06% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.71% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.86% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.40% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.86% 95.56%
CHEMBL3194 P02766 Transthyretin 88.18% 90.71%
CHEMBL1951 P21397 Monoamine oxidase A 87.79% 91.49%
CHEMBL1163101 O75460 Serine/threonine-protein kinase/endoribonuclease IRE1 86.24% 98.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.37% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 83.89% 94.73%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 82.92% 80.78%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 82.06% 85.30%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.04% 93.99%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.70% 99.17%

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.
Sideritis leucantha

Cross-Links

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PubChem 15224752
LOTUS LTS0187705
wikiData Q105299870