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[(3aS,4R,4aS,5R,8R,8aR,9R,9aS)-8,9-diacetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

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 4edca388-846b-4570-b406-8d7966dc7ec1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aS,4R,4aS,5R,8R,8aR,9R,9aS)-8,9-diacetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C(C3(C1C(CCC3OC(=O)C)(C)O)C)OC(=O)C)OC(=O)C2=C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[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/C24H32O9/c1-8-11(2)21(27)32-17-16-12(3)22(28)33-18(16)20(31-14(5)26)24(7)15(30-13(4)25)9-10-23(6,29)19(17)24/h8,15-20,29H,3,9-10H2,1-2,4-7H3/b11-8-/t15-,16+,17-,18+,19+,20+,23-,24+/m1/s1
InChI Key CGKVMMYULFGQBC-XKMKGHDTSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C24H32O9
Molecular Weight 464.50 g/mol
Exact Mass 464.20463259 g/mol
Topological Polar Surface Area (TPSA) 125.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.01
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4R,4aS,5R,8R,8aR,9R,9aS)-8,9-diacetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9910 99.10%
Caco-2 - 0.6290 62.90%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6497 64.97%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8506 85.06%
OATP1B3 inhibitior + 0.8115 81.15%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.6553 65.53%
BSEP inhibitior - 0.4936 49.36%
P-glycoprotein inhibitior + 0.7817 78.17%
P-glycoprotein substrate - 0.7707 77.07%
CYP3A4 substrate + 0.6490 64.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9170 91.70%
CYP3A4 inhibition + 0.5682 56.82%
CYP2C9 inhibition - 0.8622 86.22%
CYP2C19 inhibition - 0.8739 87.39%
CYP2D6 inhibition - 0.9481 94.81%
CYP1A2 inhibition - 0.6873 68.73%
CYP2C8 inhibition - 0.6508 65.08%
CYP inhibitory promiscuity - 0.9293 92.93%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5069 50.69%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.8719 87.19%
Skin irritation + 0.5724 57.24%
Skin corrosion - 0.8286 82.86%
Ames mutagenesis - 0.6378 63.78%
Human Ether-a-go-go-Related Gene inhibition - 0.3962 39.62%
Micronuclear - 0.7400 74.00%
Hepatotoxicity + 0.6210 62.10%
skin sensitisation - 0.7599 75.99%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.8551 85.51%
Acute Oral Toxicity (c) III 0.3784 37.84%
Estrogen receptor binding + 0.7943 79.43%
Androgen receptor binding + 0.6066 60.66%
Thyroid receptor binding + 0.5908 59.08%
Glucocorticoid receptor binding + 0.6784 67.84%
Aromatase binding + 0.6214 62.14%
PPAR gamma + 0.7833 78.33%
Honey bee toxicity - 0.7072 70.72%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9791 97.91%

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 96.38% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.33% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.01% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 94.01% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.96% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.27% 95.56%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.25% 93.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.15% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.95% 91.24%
CHEMBL340 P08684 Cytochrome P450 3A4 86.07% 91.19%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.86% 97.14%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.67% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.54% 86.33%
CHEMBL1902 P62942 FK506-binding protein 1A 84.82% 97.05%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.78% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.25% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.22% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.20% 93.03%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.16% 96.09%
CHEMBL2581 P07339 Cathepsin D 83.50% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.60% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.42% 95.50%

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 163188830
LOTUS LTS0170251
wikiData Q104957799