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[(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropanoyloxy)-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-6-yl] (2R)-2-methylbutanoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 94c9fcc5-2791-475c-a6d8-93a509f9013b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropanoyloxy)-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-6-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1CC(C2(CC3C(C(C2=C1C)OC(=O)C(C)C)C(=C)C(=O)O3)C)O
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@H]1C[C@@H]([C@]2(C[C@@H]3[C@H]([C@@H](C2=C1C)OC(=O)C(C)C)C(=C)C(=O)O3)C)O
InChI InChI=1S/C24H34O7/c1-8-12(4)22(27)29-15-9-17(25)24(7)10-16-18(14(6)23(28)30-16)20(19(24)13(15)5)31-21(26)11(2)3/h11-12,15-18,20,25H,6,8-10H2,1-5,7H3/t12-,15+,16-,17+,18-,20+,24-/m1/s1
InChI Key LPHRYJJWDSKTFA-ZZTALJPYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H34O7
Molecular Weight 434.50 g/mol
Exact Mass 434.23045342 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.10
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropanoyloxy)-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-6-yl] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9973 99.73%
Caco-2 - 0.5451 54.51%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6530 65.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8540 85.40%
OATP1B3 inhibitior + 0.8571 85.71%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.7162 71.62%
P-glycoprotein inhibitior + 0.6362 63.62%
P-glycoprotein substrate - 0.6081 60.81%
CYP3A4 substrate + 0.6572 65.72%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8873 88.73%
CYP3A4 inhibition + 0.7452 74.52%
CYP2C9 inhibition - 0.6854 68.54%
CYP2C19 inhibition - 0.7919 79.19%
CYP2D6 inhibition - 0.9536 95.36%
CYP1A2 inhibition - 0.8346 83.46%
CYP2C8 inhibition + 0.4810 48.10%
CYP inhibitory promiscuity - 0.7425 74.25%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5252 52.52%
Eye corrosion - 0.9868 98.68%
Eye irritation - 0.8562 85.62%
Skin irritation - 0.5236 52.36%
Skin corrosion - 0.9172 91.72%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7272 72.72%
Micronuclear - 0.6600 66.00%
Hepatotoxicity + 0.6178 61.78%
skin sensitisation - 0.7050 70.50%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.4702 47.02%
Estrogen receptor binding + 0.7864 78.64%
Androgen receptor binding + 0.6584 65.84%
Thyroid receptor binding + 0.5473 54.73%
Glucocorticoid receptor binding + 0.7725 77.25%
Aromatase binding + 0.5301 53.01%
PPAR gamma + 0.5793 57.93%
Honey bee toxicity - 0.5497 54.97%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.95% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.04% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 93.55% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.07% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.01% 96.09%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 92.00% 96.47%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.10% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.18% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.06% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.41% 95.50%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.40% 96.61%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 86.37% 95.71%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.84% 92.62%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 85.03% 95.71%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.00% 96.95%
CHEMBL4530 P00488 Coagulation factor XIII 84.96% 96.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.16% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.60% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.45% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 82.06% 91.19%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 81.68% 98.75%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.49% 94.33%
CHEMBL2996 Q05655 Protein kinase C delta 81.04% 97.79%
CHEMBL299 P17252 Protein kinase C alpha 80.79% 98.03%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.28% 95.89%

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.
Aspilia foliosa

Cross-Links

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PubChem 162977621
LOTUS LTS0186864
wikiData Q105155185