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[(3aS,4S,4aS,5S,8S,8aS,9R,9aS)-9-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropoxy)-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate

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 be26f13f-690c-4e68-8428-3e5a1dcc5432
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aS,4S,4aS,5S,8S,8aS,9R,9aS)-9-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropoxy)-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate
SMILES (Canonical) CC(C)COC1C2C(C(C3(C1C(CCC3OC(=O)C)(C)O)C)OC(=O)C)OC(=O)C2=C
SMILES (Isomeric) CC(C)CO[C@H]1[C@H]2[C@@H]([C@@H]([C@]3([C@@H]1[C@@](CC[C@@H]3OC(=O)C)(C)O)C)OC(=O)C)OC(=O)C2=C
InChI InChI=1S/C23H34O8/c1-11(2)10-28-17-16-12(3)21(26)31-18(16)20(30-14(5)25)23(7)15(29-13(4)24)8-9-22(6,27)19(17)23/h11,15-20,27H,3,8-10H2,1-2,4-7H3/t15-,16-,17-,18-,19-,20-,22-,23+/m0/s1
InChI Key FEXGKPQUFQIACK-WLDZLKMPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H34O8
Molecular Weight 438.50 g/mol
Exact Mass 438.22536804 g/mol
Topological Polar Surface Area (TPSA) 108.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.17
H-Bond Acceptor 8
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 [(3aS,4S,4aS,5S,8S,8aS,9R,9aS)-9-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylpropoxy)-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9912 99.12%
Caco-2 - 0.5926 59.26%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7774 77.74%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8699 86.99%
OATP1B3 inhibitior + 0.8486 84.86%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6032 60.32%
BSEP inhibitior - 0.7855 78.55%
P-glycoprotein inhibitior + 0.6343 63.43%
P-glycoprotein substrate - 0.7176 71.76%
CYP3A4 substrate + 0.6566 65.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8995 89.95%
CYP3A4 inhibition - 0.5091 50.91%
CYP2C9 inhibition - 0.5056 50.56%
CYP2C19 inhibition - 0.8292 82.92%
CYP2D6 inhibition - 0.9319 93.19%
CYP1A2 inhibition - 0.7706 77.06%
CYP2C8 inhibition - 0.6967 69.67%
CYP inhibitory promiscuity - 0.8557 85.57%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5762 57.62%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.8921 89.21%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.8949 89.49%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5648 56.48%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5038 50.38%
skin sensitisation - 0.7791 77.91%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.7679 76.79%
Acute Oral Toxicity (c) III 0.5661 56.61%
Estrogen receptor binding + 0.8107 81.07%
Androgen receptor binding + 0.6427 64.27%
Thyroid receptor binding + 0.5527 55.27%
Glucocorticoid receptor binding + 0.6330 63.30%
Aromatase binding + 0.6213 62.13%
PPAR gamma + 0.7945 79.45%
Honey bee toxicity - 0.7718 77.18%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5397 53.97%
Fish aquatic toxicity + 0.9830 98.30%

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 98.94% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.86% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.60% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.12% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.13% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 91.22% 90.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.65% 85.14%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 87.67% 95.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.48% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.35% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.69% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.49% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.15% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 83.45% 91.19%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.46% 95.56%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.39% 91.24%
CHEMBL2996 Q05655 Protein kinase C delta 82.06% 97.79%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.75% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.13% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.02% 91.07%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 80.58% 95.36%
CHEMBL5028 O14672 ADAM10 80.35% 97.50%
CHEMBL299 P17252 Protein kinase C alpha 80.03% 98.03%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.00% 86.33%

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.
Sphagneticola trilobata

Cross-Links

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PubChem 162998462
LOTUS LTS0270243
wikiData Q104994256