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[6-Acetyloxy-9-hydroxy-5a,9-dimethyl-5-(2-methylbut-2-enoyloxy)-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 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 ce5f2bbe-1f56-4c8e-a025-dd9ff7794aa9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [6-acetyloxy-9-hydroxy-5a,9-dimethyl-5-(2-methylbut-2-enoyloxy)-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2C(C3C1(C(CCC3(C)O)OC(=O)C)C)OC(=O)C2=C)OC(=O)C4(C(O4)C)C
SMILES (Isomeric) CC=C(C)C(=O)OC1C(C2C(C3C1(C(CCC3(C)O)OC(=O)C)C)OC(=O)C2=C)OC(=O)C4(C(O4)C)C
InChI InChI=1S/C27H36O10/c1-9-12(2)22(29)36-21-19(35-24(31)27(8)14(4)37-27)17-13(3)23(30)34-18(17)20-25(6,32)11-10-16(26(20,21)7)33-15(5)28/h9,14,16-21,32H,3,10-11H2,1-2,4-8H3
InChI Key KTLYEGCHMYMKHO-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H36O10
Molecular Weight 520.60 g/mol
Exact Mass 520.23084734 g/mol
Topological Polar Surface Area (TPSA) 138.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.16
H-Bond Acceptor 10
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 [6-Acetyloxy-9-hydroxy-5a,9-dimethyl-5-(2-methylbut-2-enoyloxy)-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 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 + 0.9880 98.80%
Caco-2 - 0.7125 71.25%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6595 65.95%
OATP2B1 inhibitior - 0.8579 85.79%
OATP1B1 inhibitior + 0.8330 83.30%
OATP1B3 inhibitior + 0.8411 84.11%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7053 70.53%
BSEP inhibitior + 0.8000 80.00%
P-glycoprotein inhibitior + 0.8038 80.38%
P-glycoprotein substrate - 0.5913 59.13%
CYP3A4 substrate + 0.6850 68.50%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9085 90.85%
CYP3A4 inhibition + 0.6466 64.66%
CYP2C9 inhibition - 0.8260 82.60%
CYP2C19 inhibition - 0.8748 87.48%
CYP2D6 inhibition - 0.9384 93.84%
CYP1A2 inhibition - 0.7414 74.14%
CYP2C8 inhibition + 0.4770 47.70%
CYP inhibitory promiscuity - 0.9257 92.57%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4478 44.78%
Eye corrosion - 0.9869 98.69%
Eye irritation - 0.8815 88.15%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.8394 83.94%
Ames mutagenesis - 0.5942 59.42%
Human Ether-a-go-go-Related Gene inhibition - 0.5280 52.80%
Micronuclear - 0.6400 64.00%
Hepatotoxicity + 0.6302 63.02%
skin sensitisation - 0.7605 76.05%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.7196 71.96%
Acute Oral Toxicity (c) III 0.4134 41.34%
Estrogen receptor binding + 0.7790 77.90%
Androgen receptor binding + 0.6699 66.99%
Thyroid receptor binding + 0.5547 55.47%
Glucocorticoid receptor binding + 0.6887 68.87%
Aromatase binding + 0.7104 71.04%
PPAR gamma + 0.7589 75.89%
Honey bee toxicity - 0.6842 68.42%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9751 97.51%

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 96.78% 91.11%
CHEMBL2581 P07339 Cathepsin D 93.84% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.68% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.05% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.83% 97.14%
CHEMBL221 P23219 Cyclooxygenase-1 90.61% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.53% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.06% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.04% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 88.25% 93.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.67% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.69% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.50% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 85.43% 91.19%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.02% 94.45%
CHEMBL1902 P62942 FK506-binding protein 1A 84.54% 97.05%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.24% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.79% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.42% 96.09%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.90% 93.03%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.42% 95.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.27% 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 163008155
LOTUS LTS0256265
wikiData Q105145854