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methyl (1S,4R,6S,9S,10R,11S)-10-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-9-hydroxy-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 73eaa2a9-8182-4b0f-b851-c66a835fb12b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name methyl (1S,4R,6S,9S,10R,11S)-10-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-9-hydroxy-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
SMILES (Canonical) CC1C(O1)(C)C(=O)OC2C3C(C=C(C4C(O4)C=C(C2O)C(=O)OC)C)OC(=O)C3=C
SMILES (Isomeric) C[C@@H]1[C@@](O1)(C)C(=O)O[C@@H]2[C@@H]3[C@H](C=C([C@@H]4[C@@H](O4)C=C([C@@H]2O)C(=O)OC)C)OC(=O)C3=C
InChI InChI=1S/C21H24O9/c1-8-6-12-14(9(2)18(23)28-12)17(29-20(25)21(4)10(3)30-21)15(22)11(19(24)26-5)7-13-16(8)27-13/h6-7,10,12-17,22H,2H2,1,3-5H3/t10-,12+,13+,14+,15+,16-,17-,21+/m1/s1
InChI Key ZFFQDPLDTMMAKO-OPYZLHHXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H24O9
Molecular Weight 420.40 g/mol
Exact Mass 420.14203234 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 0.36
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4R,6S,9S,10R,11S)-10-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-9-hydroxy-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9680 96.80%
Caco-2 - 0.6601 66.01%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.6082 60.82%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8241 82.41%
OATP1B3 inhibitior + 0.9123 91.23%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.8332 83.32%
P-glycoprotein inhibitior + 0.6025 60.25%
P-glycoprotein substrate - 0.5499 54.99%
CYP3A4 substrate + 0.6745 67.45%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8840 88.40%
CYP3A4 inhibition - 0.5832 58.32%
CYP2C9 inhibition - 0.9160 91.60%
CYP2C19 inhibition - 0.8460 84.60%
CYP2D6 inhibition - 0.9357 93.57%
CYP1A2 inhibition - 0.8219 82.19%
CYP2C8 inhibition - 0.5590 55.90%
CYP inhibitory promiscuity - 0.8982 89.82%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8943 89.43%
Carcinogenicity (trinary) Danger 0.4862 48.62%
Eye corrosion - 0.9555 95.55%
Eye irritation - 0.8767 87.67%
Skin irritation - 0.6822 68.22%
Skin corrosion - 0.9294 92.94%
Ames mutagenesis - 0.5554 55.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5565 55.65%
Micronuclear + 0.5500 55.00%
Hepatotoxicity + 0.6250 62.50%
skin sensitisation - 0.6667 66.67%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.5333 53.33%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.3675 36.75%
Estrogen receptor binding + 0.7765 77.65%
Androgen receptor binding + 0.5646 56.46%
Thyroid receptor binding + 0.6554 65.54%
Glucocorticoid receptor binding + 0.7464 74.64%
Aromatase binding + 0.5294 52.94%
PPAR gamma + 0.6367 63.67%
Honey bee toxicity - 0.7315 73.15%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.8725 87.25%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.78% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.43% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 92.06% 90.17%
CHEMBL3401 O75469 Pregnane X receptor 91.83% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.24% 86.33%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 87.08% 97.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.59% 91.07%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.52% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.12% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.10% 94.45%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 85.07% 81.11%
CHEMBL2581 P07339 Cathepsin D 83.85% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.79% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.86% 97.14%
CHEMBL5028 O14672 ADAM10 82.11% 97.50%
CHEMBL4208 P20618 Proteasome component C5 81.66% 90.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.34% 93.03%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.25% 85.14%
CHEMBL340 P08684 Cytochrome P450 3A4 81.07% 91.19%

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.
Melampodium leucanthum

Cross-Links

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PubChem 163015801
LOTUS LTS0189541
wikiData Q105374099