Licoleafol

Details

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Internal ID 6b370876-a1de-4ac2-be3a-5a6ab2e3cfac
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
IUPAC Name (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(E)-4-hydroxy-3-methylbut-2-enyl]-2,3-dihydrochromen-4-one
SMILES (Canonical) CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC(=C(C=C3)O)O)CO
SMILES (Isomeric) C/C(=C\CC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC(=C(C=C3)O)O)/CO
InChI InChI=1S/C20H20O7/c1-10(9-21)2-4-12-14(23)7-16(25)19-17(26)8-18(27-20(12)19)11-3-5-13(22)15(24)6-11/h2-3,5-7,18,21-25H,4,8-9H2,1H3/b10-2+/t18-/m0/s1
InChI Key CIJATEIGJFIOPE-OUOXKOSGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H20O7
Molecular Weight 372.40 g/mol
Exact Mass 372.12090297 g/mol
Topological Polar Surface Area (TPSA) 127.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.70
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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(2S)-5,7,3',4'-Tetrahydroxy-8-[(E)-3-hydroxymethyl-2-butenyl]flavanone
LMPK12140410

2D Structure

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2D Structure of Licoleafol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9348 93.48%
Caco-2 - 0.5393 53.93%
Blood Brain Barrier - 0.6201 62.01%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6418 64.18%
OATP2B1 inhibitior + 0.5580 55.80%
OATP1B1 inhibitior + 0.9118 91.18%
OATP1B3 inhibitior + 0.9724 97.24%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.5670 56.70%
P-glycoprotein inhibitior - 0.7145 71.45%
P-glycoprotein substrate - 0.8041 80.41%
CYP3A4 substrate + 0.5459 54.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8135 81.35%
CYP3A4 inhibition - 0.8377 83.77%
CYP2C9 inhibition - 0.7605 76.05%
CYP2C19 inhibition - 0.6599 65.99%
CYP2D6 inhibition - 0.8427 84.27%
CYP1A2 inhibition + 0.6041 60.41%
CYP2C8 inhibition - 0.6894 68.94%
CYP inhibitory promiscuity + 0.5491 54.91%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7255 72.55%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.5700 57.00%
Skin irritation - 0.7640 76.40%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis + 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5267 52.67%
Micronuclear - 0.5800 58.00%
Hepatotoxicity - 0.5697 56.97%
skin sensitisation - 0.8243 82.43%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.6496 64.96%
Acute Oral Toxicity (c) III 0.4425 44.25%
Estrogen receptor binding + 0.8514 85.14%
Androgen receptor binding + 0.7996 79.96%
Thyroid receptor binding + 0.6117 61.17%
Glucocorticoid receptor binding + 0.7581 75.81%
Aromatase binding - 0.5262 52.62%
PPAR gamma + 0.7593 75.93%
Honey bee toxicity - 0.8254 82.54%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9902 99.02%

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 99.42% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.15% 91.49%
CHEMBL2581 P07339 Cathepsin D 94.27% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 91.75% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.13% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.47% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.34% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.98% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.49% 96.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.42% 99.15%
CHEMBL2964 P36507 Dual specificity mitogen-activated protein kinase kinase 2 83.58% 80.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.19% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.51% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.48% 100.00%

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.
Glycyrrhiza glabra
Glycyrrhiza inflata
Glycyrrhiza uralensis
Glycyrrhiza uralensis
Mitracarpus hirtus

Cross-Links

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PubChem 11111496
NPASS NPC95933
LOTUS LTS0053828
wikiData Q76416662