[(3aR,4R,6E,9R,10E,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-acetyloxybut-2-enoate

Details

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Internal ID 6e22befb-183b-426e-a675-a4cf3ef9f10c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4R,6E,9R,10E,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-acetyloxybut-2-enoate
SMILES (Canonical) CC=C(C(=O)OC1CC(=CCC(C(=CC2C1C(=C)C(=O)O2)C)O)C)OC(=O)C
SMILES (Isomeric) C/C=C(/C(=O)O[C@@H]1C/C(=C/C[C@H](/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)/C)\OC(=O)C
InChI InChI=1S/C21H26O7/c1-6-16(26-14(5)22)21(25)28-17-9-11(2)7-8-15(23)12(3)10-18-19(17)13(4)20(24)27-18/h6-7,10,15,17-19,23H,4,8-9H2,1-3,5H3/b11-7+,12-10+,16-6-/t15-,17-,18-,19-/m1/s1
InChI Key CZGZTFUKMVHFMV-WAFGWYFRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H26O7
Molecular Weight 390.40 g/mol
Exact Mass 390.16785316 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.51
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4R,6E,9R,10E,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-acetyloxybut-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 + 0.9888 98.88%
Caco-2 + 0.6441 64.41%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.5409 54.09%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8938 89.38%
OATP1B3 inhibitior + 0.9159 91.59%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8022 80.22%
P-glycoprotein inhibitior + 0.7084 70.84%
P-glycoprotein substrate - 0.6185 61.85%
CYP3A4 substrate + 0.6406 64.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8962 89.62%
CYP3A4 inhibition - 0.7179 71.79%
CYP2C9 inhibition - 0.9302 93.02%
CYP2C19 inhibition - 0.8653 86.53%
CYP2D6 inhibition - 0.9481 94.81%
CYP1A2 inhibition - 0.7012 70.12%
CYP2C8 inhibition - 0.6103 61.03%
CYP inhibitory promiscuity - 0.9615 96.15%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5481 54.81%
Eye corrosion - 0.9526 95.26%
Eye irritation - 0.9021 90.21%
Skin irritation - 0.5845 58.45%
Skin corrosion - 0.9329 93.29%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4789 47.89%
Micronuclear - 0.6600 66.00%
Hepatotoxicity + 0.7000 70.00%
skin sensitisation - 0.7401 74.01%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.6000 60.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.7698 76.98%
Acute Oral Toxicity (c) III 0.3346 33.46%
Estrogen receptor binding + 0.6715 67.15%
Androgen receptor binding - 0.5722 57.22%
Thyroid receptor binding + 0.5311 53.11%
Glucocorticoid receptor binding + 0.8339 83.39%
Aromatase binding - 0.6571 65.71%
PPAR gamma + 0.5281 52.81%
Honey bee toxicity - 0.6513 65.13%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9794 97.94%

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 95.88% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.87% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.68% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.20% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.13% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.63% 86.33%
CHEMBL2581 P07339 Cathepsin D 82.64% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 80.79% 94.73%
CHEMBL340 P08684 Cytochrome P450 3A4 80.17% 91.19%

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.
Stevia jujuyensis

Cross-Links

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PubChem 162906164
LOTUS LTS0167882
wikiData Q104972792