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methyl (3aS,4S,5S,6E,10R,11R,11aS)-5-[(2S)-butan-2-yl]oxy-11-hydroxy-4-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-3-methylidene-2-oxospiro[4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-10,2'-oxirane]-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 c648ce5d-658f-4c70-9885-3420335d32fe
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name methyl (3aS,4S,5S,6E,10R,11R,11aS)-5-[(2S)-butan-2-yl]oxy-11-hydroxy-4-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-3-methylidene-2-oxospiro[4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-10,2'-oxirane]-6-carboxylate
SMILES (Canonical) CCC(C)OC1C(C2C(C(C3(CCC=C1C(=O)OC)CO3)O)OC(=O)C2=C)OC(=O)C(=CC)CO
SMILES (Isomeric) CC[C@H](C)O[C@@H]/1[C@H]([C@@H]2[C@@H]([C@H]([C@@]3(CC/C=C1/C(=O)OC)CO3)O)OC(=O)C2=C)OC(=O)/C(=C\C)/CO
InChI InChI=1S/C25H34O10/c1-6-13(3)33-18-16(24(30)31-5)9-8-10-25(12-32-25)21(27)20-17(14(4)22(28)35-20)19(18)34-23(29)15(7-2)11-26/h7,9,13,17-21,26-27H,4,6,8,10-12H2,1-3,5H3/b15-7-,16-9+/t13-,17+,18-,19-,20-,21+,25+/m0/s1
InChI Key HWLNMLACKWXZJJ-KTMLUWOXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H34O10
Molecular Weight 494.50 g/mol
Exact Mass 494.21519728 g/mol
Topological Polar Surface Area (TPSA) 141.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.14
H-Bond Acceptor 10
H-Bond Donor 2
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (3aS,4S,5S,6E,10R,11R,11aS)-5-[(2S)-butan-2-yl]oxy-11-hydroxy-4-[(Z)-2-(hydroxymethyl)but-2-enoyl]oxy-3-methylidene-2-oxospiro[4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-10,2'-oxirane]-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 + 0.9525 95.25%
Caco-2 - 0.6675 66.75%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.7033 70.33%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8225 82.25%
OATP1B3 inhibitior + 0.9488 94.88%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.8402 84.02%
P-glycoprotein inhibitior + 0.7253 72.53%
P-glycoprotein substrate + 0.7004 70.04%
CYP3A4 substrate + 0.6694 66.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8716 87.16%
CYP3A4 inhibition - 0.5432 54.32%
CYP2C9 inhibition - 0.7337 73.37%
CYP2C19 inhibition - 0.7929 79.29%
CYP2D6 inhibition - 0.9224 92.24%
CYP1A2 inhibition - 0.7456 74.56%
CYP2C8 inhibition + 0.4858 48.58%
CYP inhibitory promiscuity - 0.9007 90.07%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.4849 48.49%
Eye corrosion - 0.9823 98.23%
Eye irritation - 0.9169 91.69%
Skin irritation - 0.6388 63.88%
Skin corrosion - 0.9342 93.42%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6169 61.69%
Micronuclear - 0.6700 67.00%
Hepatotoxicity + 0.5024 50.24%
skin sensitisation - 0.8841 88.41%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.6423 64.23%
Acute Oral Toxicity (c) III 0.4215 42.15%
Estrogen receptor binding + 0.7768 77.68%
Androgen receptor binding + 0.5681 56.81%
Thyroid receptor binding + 0.5383 53.83%
Glucocorticoid receptor binding + 0.7845 78.45%
Aromatase binding + 0.5897 58.97%
PPAR gamma + 0.6624 66.24%
Honey bee toxicity - 0.6698 66.98%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9655 96.55%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.95% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.72% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.79% 96.09%
CHEMBL2581 P07339 Cathepsin D 95.17% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.73% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 91.42% 97.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.97% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.55% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 86.96% 94.73%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.86% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.59% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.48% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.47% 97.14%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 84.15% 98.75%
CHEMBL5028 O14672 ADAM10 83.35% 97.50%
CHEMBL221 P23219 Cyclooxygenase-1 83.26% 90.17%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.15% 95.83%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.75% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.74% 95.56%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.49% 93.03%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.01% 100.00%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 81.94% 95.71%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.61% 95.71%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.11% 92.62%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 80.90% 89.34%

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.
Tetragonotheca repanda

Cross-Links

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PubChem 162987792
LOTUS LTS0259399
wikiData Q105034699