[(1R,2R,4R,6R,9Z,11S)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] (E)-2-methylbut-2-enoate

Details

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Internal ID 46a1a4b7-1597-4dd4-93cc-f40dff4b83b3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(1R,2R,4R,6R,9Z,11S)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC2(C(O2)CCC(=CC3C1C(=C)C(=O)O3)C)C
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1C[C@@]2([C@H](O2)CC/C(=C\[C@H]3[C@@H]1C(=C)C(=O)O3)/C)C
InChI InChI=1S/C20H26O5/c1-6-12(3)18(21)24-15-10-20(5)16(25-20)8-7-11(2)9-14-17(15)13(4)19(22)23-14/h6,9,14-17H,4,7-8,10H2,1-3,5H3/b11-9-,12-6+/t14-,15+,16+,17-,20+/m0/s1
InChI Key IZTIJXKODZYJIM-WRYDFZGJSA-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) 65.10 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.25
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2R,4R,6R,9Z,11S)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] (E)-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 + 0.9845 98.45%
Caco-2 + 0.7146 71.46%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.6348 63.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8970 89.70%
OATP1B3 inhibitior + 0.8390 83.90%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.6438 64.38%
P-glycoprotein inhibitior - 0.4375 43.75%
P-glycoprotein substrate - 0.7118 71.18%
CYP3A4 substrate + 0.6733 67.33%
CYP2C9 substrate - 0.6378 63.78%
CYP2D6 substrate - 0.8830 88.30%
CYP3A4 inhibition - 0.6936 69.36%
CYP2C9 inhibition - 0.8165 81.65%
CYP2C19 inhibition - 0.8435 84.35%
CYP2D6 inhibition - 0.9483 94.83%
CYP1A2 inhibition + 0.7159 71.59%
CYP2C8 inhibition - 0.6990 69.90%
CYP inhibitory promiscuity - 0.9339 93.39%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5705 57.05%
Eye corrosion - 0.9750 97.50%
Eye irritation - 0.8965 89.65%
Skin irritation - 0.5196 51.96%
Skin corrosion - 0.8697 86.97%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7028 70.28%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.6553 65.53%
skin sensitisation - 0.7299 72.99%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.6538 65.38%
Acute Oral Toxicity (c) III 0.5122 51.22%
Estrogen receptor binding + 0.7445 74.45%
Androgen receptor binding + 0.6262 62.62%
Thyroid receptor binding + 0.5882 58.82%
Glucocorticoid receptor binding + 0.7731 77.31%
Aromatase binding + 0.5536 55.36%
PPAR gamma + 0.6683 66.83%
Honey bee toxicity - 0.6800 68.00%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.9931 99.31%

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 96.81% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.19% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.65% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.33% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.12% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.04% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.13% 96.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.85% 95.89%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 85.59% 93.03%
CHEMBL221 P23219 Cyclooxygenase-1 84.26% 90.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.23% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.46% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.25% 97.09%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.99% 93.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.74% 97.14%

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.
Calea rotundifolia

Cross-Links

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PubChem 163002089
LOTUS LTS0161798
wikiData Q105123464