Eupalinolide B

Details

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Internal ID 496e3ced-e0e7-4a2c-a684-f68a4dcf353d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4S,6E,9S,10E,11aR)-9-acetyloxy-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
SMILES (Canonical) CC1=CC2C(C(CC(=CCC1OC(=O)C)COC(=O)C)OC(=O)C(=CCO)C)C(=C)C(=O)O2
SMILES (Isomeric) C/C/1=C\[C@@H]2[C@@H]([C@H](C/C(=C\C[C@@H]1OC(=O)C)/COC(=O)C)OC(=O)/C(=C/CO)/C)C(=C)C(=O)O2
InChI InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10+,18-6+/t19-,20+,21-,22-/m0/s1
InChI Key HPWMABTYJYZFLK-GOMZETCQSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C24H30O9
Molecular Weight 462.50 g/mol
Exact Mass 462.18898253 g/mol
Topological Polar Surface Area (TPSA) 125.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 2.10
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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877822-40-7
AKOS037514641

2D Structure

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2D Structure of Eupalinolide B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9741 97.41%
Caco-2 - 0.6383 63.83%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.6584 65.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8527 85.27%
OATP1B3 inhibitior + 0.9314 93.14%
MATE1 inhibitior - 0.8212 82.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8655 86.55%
P-glycoprotein inhibitior + 0.8257 82.57%
P-glycoprotein substrate - 0.5745 57.45%
CYP3A4 substrate + 0.6675 66.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9071 90.71%
CYP3A4 inhibition - 0.5765 57.65%
CYP2C9 inhibition - 0.8679 86.79%
CYP2C19 inhibition - 0.7843 78.43%
CYP2D6 inhibition - 0.9457 94.57%
CYP1A2 inhibition - 0.6416 64.16%
CYP2C8 inhibition + 0.5241 52.41%
CYP inhibitory promiscuity - 0.8804 88.04%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.6227 62.27%
Eye corrosion - 0.9639 96.39%
Eye irritation - 0.8834 88.34%
Skin irritation - 0.6119 61.19%
Skin corrosion - 0.9243 92.43%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7649 76.49%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.5093 50.93%
skin sensitisation - 0.7391 73.91%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.7122 71.22%
Acute Oral Toxicity (c) III 0.5310 53.10%
Estrogen receptor binding + 0.8517 85.17%
Androgen receptor binding - 0.5374 53.74%
Thyroid receptor binding + 0.5218 52.18%
Glucocorticoid receptor binding + 0.8317 83.17%
Aromatase binding + 0.5549 55.49%
PPAR gamma + 0.6497 64.97%
Honey bee toxicity - 0.6493 64.93%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9502 95.02%

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 96.53% 91.11%
CHEMBL2581 P07339 Cathepsin D 89.51% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.27% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.12% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.93% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 86.19% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.87% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.86% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.84% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.32% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.22% 99.23%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 80.67% 96.39%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.41% 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.
Eupatorium lindleyanum

Cross-Links

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PubChem 102004890
NPASS NPC107996