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[(3aS,4S,5R,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

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 3fd32119-b7df-40fb-a35c-d7c4ad407fc7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aS,4S,5R,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2C(C3C1(C(CC=C3C)O)C)OC(=O)C2=C)OC(=O)C4(C(O4)C)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@H]([C@@H]2[C@H]([C@@H]3[C@@]1([C@@H](CC=C3C)O)C)OC(=O)C2=C)OC(=O)[C@@]4([C@H](O4)C)C
InChI InChI=1S/C25H32O8/c1-8-11(2)21(27)32-20-19(31-23(29)25(7)14(5)33-25)16-13(4)22(28)30-18(16)17-12(3)9-10-15(26)24(17,20)6/h8-9,14-20,26H,4,10H2,1-3,5-7H3/b11-8-/t14-,15-,16+,17-,18-,19+,20+,24+,25+/m1/s1
InChI Key YENZYUNQMNUYBV-WSDYYAPKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H32O8
Molecular Weight 460.50 g/mol
Exact Mass 460.20971797 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.40
H-Bond Acceptor 8
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,4S,5R,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9890 98.90%
Caco-2 - 0.5814 58.14%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6267 62.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8525 85.25%
OATP1B3 inhibitior + 0.8861 88.61%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.6106 61.06%
P-glycoprotein inhibitior + 0.7442 74.42%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6669 66.69%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8793 87.93%
CYP3A4 inhibition + 0.5520 55.20%
CYP2C9 inhibition - 0.9379 93.79%
CYP2C19 inhibition - 0.8940 89.40%
CYP2D6 inhibition - 0.9361 93.61%
CYP1A2 inhibition - 0.8828 88.28%
CYP2C8 inhibition - 0.5882 58.82%
CYP inhibitory promiscuity - 0.8841 88.41%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Danger 0.4174 41.74%
Eye corrosion - 0.9812 98.12%
Eye irritation - 0.9055 90.55%
Skin irritation - 0.5894 58.94%
Skin corrosion - 0.8942 89.42%
Ames mutagenesis - 0.6296 62.96%
Human Ether-a-go-go-Related Gene inhibition - 0.4624 46.24%
Micronuclear - 0.5141 51.41%
Hepatotoxicity + 0.7334 73.34%
skin sensitisation - 0.6493 64.93%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.5607 56.07%
Acute Oral Toxicity (c) III 0.4128 41.28%
Estrogen receptor binding + 0.7647 76.47%
Androgen receptor binding + 0.6808 68.08%
Thyroid receptor binding + 0.6234 62.34%
Glucocorticoid receptor binding + 0.6843 68.43%
Aromatase binding + 0.5847 58.47%
PPAR gamma + 0.6692 66.92%
Honey bee toxicity - 0.6270 62.70%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9655 96.55%

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 97.12% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.04% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 96.02% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.37% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.31% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.27% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.45% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.44% 91.07%
CHEMBL3359 P21462 Formyl peptide receptor 1 88.37% 93.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.47% 97.25%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.41% 95.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.41% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.39% 97.21%
CHEMBL3401 O75469 Pregnane X receptor 85.37% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.10% 97.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.31% 94.45%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 84.20% 85.30%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.97% 94.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.36% 93.03%
CHEMBL340 P08684 Cytochrome P450 3A4 81.91% 91.19%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.51% 93.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.50% 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.
Calostephane divaricata

Cross-Links

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PubChem 163086991
LOTUS LTS0035321
wikiData Q105347327