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methyl (3aR,4S,5S,6E,10Z,11aS)-10-(acetyloxymethyl)-4-[(2R,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-5-hydroxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-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 7fa4a7f3-d7af-46cf-a6bf-0eba58c0f087
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name methyl (3aR,4S,5S,6E,10Z,11aS)-10-(acetyloxymethyl)-4-[(2R,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-5-hydroxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
SMILES (Canonical) CC1C(O1)(C)C(=O)OC2C3C(C=C(CCC=C(C2O)C(=O)OC)COC(=O)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(/CC/C=C(\[C@@H]2O)/C(=O)OC)\COC(=O)C)OC(=O)C3=C
InChI InChI=1S/C23H28O10/c1-11-17-16(31-20(11)26)9-14(10-30-13(3)24)7-6-8-15(21(27)29-5)18(25)19(17)32-22(28)23(4)12(2)33-23/h8-9,12,16-19,25H,1,6-7,10H2,2-5H3/b14-9-,15-8+/t12-,16+,17-,18+,19+,23-/m1/s1
InChI Key PDLXQJMKWOQPKU-CSUKRJLFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H28O10
Molecular Weight 464.50 g/mol
Exact Mass 464.16824709 g/mol
Topological Polar Surface Area (TPSA) 138.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 0.92
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (3aR,4S,5S,6E,10Z,11aS)-10-(acetyloxymethyl)-4-[(2R,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-5-hydroxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9457 94.57%
Caco-2 - 0.7469 74.69%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7223 72.23%
OATP2B1 inhibitior - 0.8598 85.98%
OATP1B1 inhibitior + 0.8246 82.46%
OATP1B3 inhibitior + 0.9489 94.89%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6771 67.71%
BSEP inhibitior + 0.7348 73.48%
P-glycoprotein inhibitior + 0.7081 70.81%
P-glycoprotein substrate + 0.5346 53.46%
CYP3A4 substrate + 0.6925 69.25%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8960 89.60%
CYP3A4 inhibition - 0.7101 71.01%
CYP2C9 inhibition - 0.7520 75.20%
CYP2C19 inhibition - 0.8070 80.70%
CYP2D6 inhibition - 0.9077 90.77%
CYP1A2 inhibition - 0.6469 64.69%
CYP2C8 inhibition + 0.5564 55.64%
CYP inhibitory promiscuity - 0.8608 86.08%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.5138 51.38%
Eye corrosion - 0.9718 97.18%
Eye irritation - 0.9399 93.99%
Skin irritation - 0.6203 62.03%
Skin corrosion - 0.9179 91.79%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6276 62.76%
Micronuclear - 0.6400 64.00%
Hepatotoxicity - 0.5416 54.16%
skin sensitisation - 0.7799 77.99%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.6364 63.64%
Acute Oral Toxicity (c) III 0.4465 44.65%
Estrogen receptor binding + 0.7531 75.31%
Androgen receptor binding + 0.5681 56.81%
Thyroid receptor binding + 0.6029 60.29%
Glucocorticoid receptor binding + 0.8473 84.73%
Aromatase binding + 0.5822 58.22%
PPAR gamma + 0.5588 55.88%
Honey bee toxicity - 0.6885 68.85%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9485 94.85%

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 99.91% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.74% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.51% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.72% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 92.80% 90.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.39% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.28% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.60% 86.33%
CHEMBL2581 P07339 Cathepsin D 88.02% 98.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.42% 91.07%
CHEMBL299 P17252 Protein kinase C alpha 85.79% 98.03%
CHEMBL340 P08684 Cytochrome P450 3A4 85.41% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.03% 97.09%
CHEMBL4208 P20618 Proteasome component C5 83.92% 90.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.85% 99.17%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.78% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.44% 99.23%
CHEMBL5028 O14672 ADAM10 82.37% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.28% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 81.33% 92.50%
CHEMBL2996 Q05655 Protein kinase C delta 80.69% 97.79%

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 longipilum

Cross-Links

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PubChem 162992840
LOTUS LTS0070198
wikiData Q105206602