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

Details

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Internal ID 8883b71e-5569-4162-8450-60517887ed0f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4R,6aR,7S,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(=C)C2C(C=C(C2C3C1C(=C)C(=O)O3)C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1CC(=C)[C@@H]2[C@H](C=C([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C)O
InChI InChI=1S/C20H24O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6-7,13-18,21H,4-5,8H2,1-3H3/b9-6-/t13-,14+,15+,16-,17+,18+/m0/s1
InChI Key JEAWGNYMYMHNGM-LSLHFRIISA-N
Popularity 3 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 2.10
Atomic LogP (AlogP) 2.48
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4R,6aR,7S,9aR,9bR)-7-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-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 + 0.9700 97.00%
Caco-2 - 0.5230 52.30%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6018 60.18%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8789 87.89%
OATP1B3 inhibitior + 0.9223 92.23%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.7790 77.90%
P-glycoprotein inhibitior - 0.6289 62.89%
P-glycoprotein substrate - 0.7776 77.76%
CYP3A4 substrate + 0.6036 60.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8778 87.78%
CYP3A4 inhibition - 0.7172 71.72%
CYP2C9 inhibition - 0.8786 87.86%
CYP2C19 inhibition - 0.8200 82.00%
CYP2D6 inhibition - 0.9487 94.87%
CYP1A2 inhibition - 0.7667 76.67%
CYP2C8 inhibition - 0.7473 74.73%
CYP inhibitory promiscuity - 0.8574 85.74%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9368 93.68%
Carcinogenicity (trinary) Non-required 0.4672 46.72%
Eye corrosion - 0.9284 92.84%
Eye irritation - 0.7994 79.94%
Skin irritation - 0.6557 65.57%
Skin corrosion - 0.9173 91.73%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4447 44.47%
Micronuclear + 0.5100 51.00%
Hepatotoxicity + 0.7033 70.33%
skin sensitisation - 0.7341 73.41%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.7869 78.69%
Acute Oral Toxicity (c) II 0.5275 52.75%
Estrogen receptor binding + 0.5536 55.36%
Androgen receptor binding - 0.5298 52.98%
Thyroid receptor binding + 0.5232 52.32%
Glucocorticoid receptor binding - 0.5772 57.72%
Aromatase binding - 0.6781 67.81%
PPAR gamma - 0.5558 55.58%
Honey bee toxicity - 0.6330 63.30%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9267 92.67%

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 95.11% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.49% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.59% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 89.52% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.27% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.94% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 85.79% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.77% 89.00%
CHEMBL2581 P07339 Cathepsin D 82.99% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.05% 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.
Helianthus annuus

Cross-Links

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PubChem 102445834
LOTUS LTS0222517
wikiData Q105125912