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[(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate

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 1c894e0c-d313-4ab7-9773-9f18d984e61b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C25H30O9/c1-5-14(9-26)23(29)31-10-15(6-2)24(30)33-17-8-25(11-32-25)20-16(27)7-12(3)18(20)21-19(17)13(4)22(28)34-21/h5-7,16-21,26-27H,4,8-11H2,1-3H3/b14-5+,15-6+/t16-,17-,18+,19-,20-,21-,25+/m1/s1
InChI Key OJGCMHDRPRMYPP-XUURKMTHSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C25H30O9
Molecular Weight 474.50 g/mol
Exact Mass 474.18898253 g/mol
Topological Polar Surface Area (TPSA) 132.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.15
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-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 + 0.9249 92.49%
Caco-2 - 0.7599 75.99%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6776 67.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8767 87.67%
OATP1B3 inhibitior + 0.9477 94.77%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8504 85.04%
P-glycoprotein inhibitior + 0.6026 60.26%
P-glycoprotein substrate + 0.5226 52.26%
CYP3A4 substrate + 0.6672 66.72%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8716 87.16%
CYP3A4 inhibition - 0.8149 81.49%
CYP2C9 inhibition - 0.8350 83.50%
CYP2C19 inhibition - 0.8201 82.01%
CYP2D6 inhibition - 0.9313 93.13%
CYP1A2 inhibition - 0.7772 77.72%
CYP2C8 inhibition + 0.4574 45.74%
CYP inhibitory promiscuity - 0.8950 89.50%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5879 58.79%
Eye corrosion - 0.9776 97.76%
Eye irritation - 0.9392 93.92%
Skin irritation - 0.6670 66.70%
Skin corrosion - 0.9260 92.60%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7308 73.08%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.6428 64.28%
skin sensitisation - 0.7776 77.76%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.6444 64.44%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.8591 85.91%
Acute Oral Toxicity (c) III 0.3210 32.10%
Estrogen receptor binding + 0.7441 74.41%
Androgen receptor binding + 0.6772 67.72%
Thyroid receptor binding - 0.4881 48.81%
Glucocorticoid receptor binding + 0.7486 74.86%
Aromatase binding + 0.6044 60.44%
PPAR gamma + 0.5846 58.46%
Honey bee toxicity - 0.6644 66.44%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9724 97.24%

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 97.55% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.49% 91.11%
CHEMBL2996 Q05655 Protein kinase C delta 93.27% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.06% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.45% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.97% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.91% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.62% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 88.77% 94.73%
CHEMBL4040 P28482 MAP kinase ERK2 87.74% 83.82%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 85.74% 89.34%
CHEMBL2581 P07339 Cathepsin D 85.45% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.77% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.72% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.50% 100.00%
CHEMBL5028 O14672 ADAM10 81.79% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.00% 99.23%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.97% 98.75%
CHEMBL221 P23219 Cyclooxygenase-1 80.87% 90.17%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.69% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.12% 93.03%

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.
Liatris squarrosa

Cross-Links

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PubChem 162907318
LOTUS LTS0244401
wikiData Q105193066