[(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate

Details

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Internal ID 2a55ef3f-3119-4a72-bd7f-4c2e01402296
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
SMILES (Canonical) CC1=CCC2C1C3C(C(CC2=C)OC(=O)C(=CCO)C)C(=C)C(=O)O3
SMILES (Isomeric) CC1=CC[C@@H]2[C@H]1[C@@H]3[C@@H]([C@@H](CC2=C)OC(=O)/C(=C/CO)/C)C(=C)C(=O)O3
InChI InChI=1S/C20H24O5/c1-10-5-6-14-12(3)9-15(24-19(22)11(2)7-8-21)17-13(4)20(23)25-18(17)16(10)14/h5,7,14-18,21H,3-4,6,8-9H2,1-2H3/b11-7+/t14-,15+,16-,17+,18+/m0/s1
InChI Key IEGGJIUEFMTJED-VFHVBBQNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H24O5
Molecular Weight 344.40 g/mol
Exact Mass 344.16237386 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.48
H-Bond Acceptor 5
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,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-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 + 0.9836 98.36%
Caco-2 + 0.5589 55.89%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.6346 63.46%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8971 89.71%
OATP1B3 inhibitior + 0.9372 93.72%
MATE1 inhibitior - 0.8012 80.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.6940 69.40%
P-glycoprotein inhibitior - 0.5431 54.31%
P-glycoprotein substrate - 0.7557 75.57%
CYP3A4 substrate + 0.6205 62.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8868 88.68%
CYP3A4 inhibition - 0.6049 60.49%
CYP2C9 inhibition - 0.8518 85.18%
CYP2C19 inhibition - 0.8263 82.63%
CYP2D6 inhibition - 0.9407 94.07%
CYP1A2 inhibition - 0.6326 63.26%
CYP2C8 inhibition - 0.7229 72.29%
CYP inhibitory promiscuity - 0.8552 85.52%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.6863 68.63%
Eye corrosion - 0.9624 96.24%
Eye irritation - 0.8353 83.53%
Skin irritation - 0.6218 62.18%
Skin corrosion - 0.9135 91.35%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6743 67.43%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.5322 53.22%
skin sensitisation - 0.7459 74.59%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.5273 52.73%
Acute Oral Toxicity (c) II 0.4411 44.11%
Estrogen receptor binding + 0.7646 76.46%
Androgen receptor binding + 0.5790 57.90%
Thyroid receptor binding + 0.5324 53.24%
Glucocorticoid receptor binding + 0.5888 58.88%
Aromatase binding + 0.5739 57.39%
PPAR gamma + 0.5393 53.93%
Honey bee toxicity - 0.7157 71.57%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9647 96.47%

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 94.26% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.82% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 90.62% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.13% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 86.66% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.53% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.09% 94.45%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.99% 93.56%
CHEMBL2581 P07339 Cathepsin D 83.19% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.43% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.12% 89.00%

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.
Stevia chamaedrys
Stevia mercedensis

Cross-Links

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PubChem 13994648
LOTUS LTS0030520
wikiData Q105111757