[(E)-2-[[(3aR,4R,6E,9S,10Z,11aS)-9-hydroxy-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

Top
Internal ID bbf9a6f4-340b-492a-8ce6-53af5f9baf70
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(E)-2-[[(3aR,4R,6E,9S,10Z,11aS)-9-hydroxy-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(=CCC(C(=CC2C1C(=C)C(=O)O2)C)O)C
SMILES (Isomeric) C/C=C(\CO)/C(=O)OC/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
InChI InChI=1S/C25H32O8/c1-6-17(12-26)24(29)31-13-18(7-2)25(30)33-20-10-14(3)8-9-19(27)15(4)11-21-22(20)16(5)23(28)32-21/h6-8,11,19-22,26-27H,5,9-10,12-13H2,1-4H3/b14-8+,15-11-,17-6+,18-7+/t19-,20+,21-,22+/m0/s1
InChI Key VZIHXHDXSDCOCX-HIYXSJGXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C25H32O8
Molecular Weight 460.50 g/mol
Exact Mass 460.20971797 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.47
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(E)-2-[[(3aR,4R,6E,9S,10Z,11aS)-9-hydroxy-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

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9793 97.93%
Caco-2 - 0.7039 70.39%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6550 65.50%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8904 89.04%
OATP1B3 inhibitior + 0.9449 94.49%
MATE1 inhibitior - 0.8612 86.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8786 87.86%
P-glycoprotein inhibitior + 0.7721 77.21%
P-glycoprotein substrate - 0.5268 52.68%
CYP3A4 substrate + 0.6373 63.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8800 88.00%
CYP3A4 inhibition - 0.6727 67.27%
CYP2C9 inhibition - 0.8958 89.58%
CYP2C19 inhibition - 0.8386 83.86%
CYP2D6 inhibition - 0.9295 92.95%
CYP1A2 inhibition - 0.6766 67.66%
CYP2C8 inhibition - 0.5955 59.55%
CYP inhibitory promiscuity - 0.9341 93.41%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.6527 65.27%
Eye corrosion - 0.9754 97.54%
Eye irritation - 0.9327 93.27%
Skin irritation - 0.6519 65.19%
Skin corrosion - 0.9427 94.27%
Ames mutagenesis - 0.7154 71.54%
Human Ether-a-go-go-Related Gene inhibition + 0.6637 66.37%
Micronuclear - 0.8000 80.00%
Hepatotoxicity + 0.6000 60.00%
skin sensitisation - 0.8260 82.60%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity + 0.5875 58.75%
Acute Oral Toxicity (c) III 0.5202 52.02%
Estrogen receptor binding + 0.6560 65.60%
Androgen receptor binding + 0.5216 52.16%
Thyroid receptor binding + 0.5313 53.13%
Glucocorticoid receptor binding + 0.7907 79.07%
Aromatase binding - 0.5366 53.66%
PPAR gamma - 0.6066 60.66%
Honey bee toxicity - 0.7091 70.91%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9789 97.89%

Targets

Top

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 95.35% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.89% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.42% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.15% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 90.41% 94.73%
CHEMBL2581 P07339 Cathepsin D 85.07% 98.95%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 84.70% 97.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.17% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.05% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.89% 89.00%
CHEMBL2996 Q05655 Protein kinase C delta 82.45% 97.79%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.36% 96.09%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.90% 93.03%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.15% 95.89%
CHEMBL5028 O14672 ADAM10 80.85% 97.50%

Plants that contains it

Top
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.
Ageratina saltillensis
Liatris cylindracea

Cross-Links

Top
PubChem 162908342
LOTUS LTS0185450
wikiData Q105299779