[(E)-2-[[(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl]oxycarbonyl]but-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate

Details

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Internal ID f3043973-4852-4dfa-95d9-237e032c83d5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(E)-2-[[(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl]oxycarbonyl]but-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate
SMILES (Canonical) CC=C(CO)C(=O)OCC(=CC)C(=O)OC1CC(=CCCC(=CC2C1C(=C)C(=O)O2)C)C
SMILES (Isomeric) C/C=C(\CO)/C(=O)OC/C(=C\C)/C(=O)O[C@@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)/C
InChI InChI=1S/C25H32O7/c1-6-18(13-26)24(28)30-14-19(7-2)25(29)32-21-12-16(4)10-8-9-15(3)11-20-22(21)17(5)23(27)31-20/h6-7,10-11,20-22,26H,5,8-9,12-14H2,1-4H3/b15-11+,16-10+,18-6+,19-7+/t20-,21-,22+/m1/s1
InChI Key MZDDYPUIJFFVAN-PSXPACFMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H32O7
Molecular Weight 444.50 g/mol
Exact Mass 444.21480336 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.50
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(E)-2-[[(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl]oxycarbonyl]but-2-enyl] (E)-2-(hydroxymethyl)but-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 + 0.9721 97.21%
Caco-2 - 0.6055 60.55%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6781 67.81%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9018 90.18%
OATP1B3 inhibitior + 0.9067 90.67%
MATE1 inhibitior - 0.8012 80.12%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.9239 92.39%
P-glycoprotein inhibitior + 0.8307 83.07%
P-glycoprotein substrate - 0.6772 67.72%
CYP3A4 substrate + 0.6260 62.60%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8868 88.68%
CYP3A4 inhibition + 0.5102 51.02%
CYP2C9 inhibition - 0.8655 86.55%
CYP2C19 inhibition - 0.8004 80.04%
CYP2D6 inhibition - 0.9262 92.62%
CYP1A2 inhibition + 0.5080 50.80%
CYP2C8 inhibition - 0.5591 55.91%
CYP inhibitory promiscuity - 0.9361 93.61%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6635 66.35%
Eye corrosion - 0.9741 97.41%
Eye irritation - 0.9248 92.48%
Skin irritation - 0.5466 54.66%
Skin corrosion - 0.9406 94.06%
Ames mutagenesis - 0.6654 66.54%
Human Ether-a-go-go-Related Gene inhibition + 0.6714 67.14%
Micronuclear - 0.8800 88.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.8652 86.52%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity + 0.5985 59.85%
Acute Oral Toxicity (c) III 0.6189 61.89%
Estrogen receptor binding + 0.5918 59.18%
Androgen receptor binding + 0.5905 59.05%
Thyroid receptor binding + 0.5372 53.72%
Glucocorticoid receptor binding + 0.7610 76.10%
Aromatase binding - 0.4903 49.03%
PPAR gamma - 0.5287 52.87%
Honey bee toxicity - 0.7440 74.40%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9791 97.91%

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 97.17% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.69% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.94% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.44% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 90.96% 94.73%
CHEMBL2996 Q05655 Protein kinase C delta 88.00% 97.79%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.88% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.90% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.45% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.38% 96.09%
CHEMBL2581 P07339 Cathepsin D 84.30% 98.95%
CHEMBL5028 O14672 ADAM10 81.84% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.74% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.13% 95.89%

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.
Brickellia secundiflora
Eupatoriastrum nelsonii
Koanophyllon monanthum

Cross-Links

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PubChem 14109667
LOTUS LTS0145780
wikiData Q105175367