[3-Methylidene-2-oxo-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-5a-yl]methyl 2-methylbut-2-enoate

Details

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Internal ID 2aced655-c9d0-48ce-ba9d-9f2c3dd58f46
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
IUPAC Name [3-methylidene-2-oxo-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-5a-yl]methyl 2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OCC12CC3C(CC1C2CCC(=O)C)C(=C)C(=O)O3
SMILES (Isomeric) CC=C(C)C(=O)OCC12CC3C(CC1C2CCC(=O)C)C(=C)C(=O)O3
InChI InChI=1S/C20H26O5/c1-5-11(2)18(22)24-10-20-9-17-14(13(4)19(23)25-17)8-16(20)15(20)7-6-12(3)21/h5,14-17H,4,6-10H2,1-3H3
InChI Key SSGAUUVMLMPVHR-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O5
Molecular Weight 346.40 g/mol
Exact Mass 346.17802393 g/mol
Topological Polar Surface Area (TPSA) 69.70 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.99
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [3-Methylidene-2-oxo-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-5a-yl]methyl 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 + 0.9906 99.06%
Caco-2 + 0.5287 52.87%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7162 71.62%
OATP2B1 inhibitior - 0.8605 86.05%
OATP1B1 inhibitior + 0.8500 85.00%
OATP1B3 inhibitior + 0.9350 93.50%
MATE1 inhibitior - 0.5800 58.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior - 0.6198 61.98%
P-glycoprotein inhibitior - 0.5135 51.35%
P-glycoprotein substrate - 0.7396 73.96%
CYP3A4 substrate + 0.6478 64.78%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9102 91.02%
CYP3A4 inhibition - 0.6656 66.56%
CYP2C9 inhibition - 0.7752 77.52%
CYP2C19 inhibition - 0.7853 78.53%
CYP2D6 inhibition - 0.9354 93.54%
CYP1A2 inhibition - 0.5518 55.18%
CYP2C8 inhibition - 0.5919 59.19%
CYP inhibitory promiscuity - 0.7596 75.96%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6406 64.06%
Eye corrosion - 0.9841 98.41%
Eye irritation - 0.8828 88.28%
Skin irritation - 0.5810 58.10%
Skin corrosion - 0.9346 93.46%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4301 43.01%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.6735 67.35%
skin sensitisation - 0.7530 75.30%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.6467 64.67%
Acute Oral Toxicity (c) III 0.6254 62.54%
Estrogen receptor binding + 0.6873 68.73%
Androgen receptor binding + 0.5716 57.16%
Thyroid receptor binding - 0.6374 63.74%
Glucocorticoid receptor binding + 0.7705 77.05%
Aromatase binding - 0.5840 58.40%
PPAR gamma + 0.5498 54.98%
Honey bee toxicity - 0.6192 61.92%
Biodegradation - 0.6000 60.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9971 99.71%

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 95.57% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.11% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.58% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.68% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.08% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.69% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.62% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.48% 89.00%
CHEMBL299 P17252 Protein kinase C alpha 85.27% 98.03%
CHEMBL221 P23219 Cyclooxygenase-1 84.83% 90.17%
CHEMBL2996 Q05655 Protein kinase C delta 82.62% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.69% 86.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.66% 91.24%

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.
Geigeria ornativa

Cross-Links

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PubChem 163040154
LOTUS LTS0066547
wikiData Q105259648