[(1S,2R,6R,7R,9R,10S,11S,12R,14S)-11-acetyloxy-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecan-7-yl] (E)-4-hydroxy-2-methylbut-2-enoate

Details

Top
Internal ID 49c9626a-b5d7-4245-b7db-2c0ec3d65ff9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
IUPAC Name [(1S,2R,6R,7R,9R,10S,11S,12R,14S)-11-acetyloxy-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecan-7-yl] (E)-4-hydroxy-2-methylbut-2-enoate
SMILES (Canonical) CC(=CCO)C(=O)OC1CC(C2C(C3C1C(=C)C(=O)O3)C4(C(C2OC(=O)C)O4)C)(CO)O
SMILES (Isomeric) C/C(=C\CO)/C(=O)O[C@@H]1C[C@@]([C@H]2[C@@H]([C@H]3[C@@H]1C(=C)C(=O)O3)[C@]4([C@@H]([C@H]2OC(=O)C)O4)C)(CO)O
InChI InChI=1S/C22H28O10/c1-9(5-6-23)19(26)30-12-7-22(28,8-24)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,23-24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16-,17+,18-,21+,22+/m1/s1
InChI Key XXDDPYGIIXZQBL-LSGPNRSSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H28O10
Molecular Weight 452.50 g/mol
Exact Mass 452.16824709 g/mol
Topological Polar Surface Area (TPSA) 152.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -0.60
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(1S,2R,6R,7R,9R,10S,11S,12R,14S)-11-acetyloxy-9-hydroxy-9-(hydroxymethyl)-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecan-7-yl] (E)-4-hydroxy-2-methylbut-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8902 89.02%
Caco-2 - 0.7448 74.48%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6593 65.93%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8691 86.91%
OATP1B3 inhibitior + 0.9339 93.39%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.6992 69.92%
P-glycoprotein inhibitior - 0.4845 48.45%
P-glycoprotein substrate - 0.5731 57.31%
CYP3A4 substrate + 0.6844 68.44%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9000 90.00%
CYP3A4 inhibition - 0.7362 73.62%
CYP2C9 inhibition - 0.8758 87.58%
CYP2C19 inhibition - 0.8415 84.15%
CYP2D6 inhibition - 0.9303 93.03%
CYP1A2 inhibition - 0.8459 84.59%
CYP2C8 inhibition - 0.6054 60.54%
CYP inhibitory promiscuity - 0.9513 95.13%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6768 67.68%
Eye corrosion - 0.9821 98.21%
Eye irritation - 0.9097 90.97%
Skin irritation - 0.6896 68.96%
Skin corrosion - 0.9164 91.64%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4522 45.22%
Micronuclear - 0.6341 63.41%
Hepatotoxicity + 0.5647 56.47%
skin sensitisation - 0.7767 77.67%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.7532 75.32%
Acute Oral Toxicity (c) III 0.4112 41.12%
Estrogen receptor binding + 0.7602 76.02%
Androgen receptor binding + 0.6795 67.95%
Thyroid receptor binding + 0.5802 58.02%
Glucocorticoid receptor binding + 0.7603 76.03%
Aromatase binding + 0.5586 55.86%
PPAR gamma + 0.6312 63.12%
Honey bee toxicity - 0.5912 59.12%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.8275 82.75%

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 98.02% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.81% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 95.72% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.19% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.81% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.75% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.73% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 85.84% 97.79%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.52% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.45% 89.00%
CHEMBL4040 P28482 MAP kinase ERK2 84.28% 83.82%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.37% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.15% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.82% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.79% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.63% 99.23%

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.
Eupatorium lindleyanum

Cross-Links

Top
PubChem 163072964
LOTUS LTS0179641
wikiData Q105343971