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[(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-6-(3-methylbut-2-enoyloxy)-3-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-4-yl] (E)-2-methylbut-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 b750a2dd-d011-4717-8058-d9cccc8c978b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-6-(3-methylbut-2-enoyloxy)-3-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-4-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(CC3(C1=C(C(CC3O)OC(=O)C=C(C)C)C)C)OC(=O)C2=C
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@H]1[C@H]2[C@@H](C[C@]3(C1=C([C@H](C[C@@H]3O)OC(=O)C=C(C)C)C)C)OC(=O)C2=C
InChI InChI=1S/C25H32O7/c1-8-13(4)23(28)32-22-20-15(6)24(29)31-17(20)11-25(7)18(26)10-16(14(5)21(22)25)30-19(27)9-12(2)3/h8-9,16-18,20,22,26H,6,10-11H2,1-5,7H3/b13-8+/t16-,17+,18-,20+,22-,25+/m0/s1
InChI Key JDCRIYVAJINLGR-WSVSXHBLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H32O7
Molecular Weight 444.50 g/mol
Exact Mass 444.21480336 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.33
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,6S,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-6-(3-methylbut-2-enoyloxy)-3-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-4-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 + 0.9958 99.58%
Caco-2 - 0.5417 54.17%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.7248 72.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8774 87.74%
OATP1B3 inhibitior - 0.2453 24.53%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.4549 45.49%
P-glycoprotein inhibitior + 0.7995 79.95%
P-glycoprotein substrate - 0.5383 53.83%
CYP3A4 substrate + 0.6815 68.15%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9042 90.42%
CYP3A4 inhibition + 0.5979 59.79%
CYP2C9 inhibition - 0.7490 74.90%
CYP2C19 inhibition - 0.8734 87.34%
CYP2D6 inhibition - 0.9594 95.94%
CYP1A2 inhibition - 0.7829 78.29%
CYP2C8 inhibition + 0.5158 51.58%
CYP inhibitory promiscuity - 0.8871 88.71%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.4997 49.97%
Eye corrosion - 0.9856 98.56%
Eye irritation - 0.8874 88.74%
Skin irritation - 0.5359 53.59%
Skin corrosion - 0.9117 91.17%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6951 69.51%
Micronuclear - 0.6200 62.00%
Hepatotoxicity + 0.7000 70.00%
skin sensitisation - 0.6872 68.72%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.8324 83.24%
Acute Oral Toxicity (c) I 0.4154 41.54%
Estrogen receptor binding + 0.7318 73.18%
Androgen receptor binding + 0.6182 61.82%
Thyroid receptor binding + 0.5895 58.95%
Glucocorticoid receptor binding + 0.8556 85.56%
Aromatase binding + 0.5763 57.63%
PPAR gamma + 0.6824 68.24%
Honey bee toxicity + 0.6188 61.88%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.7000 70.00%
Fish aquatic toxicity + 0.9974 99.74%

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 95.41% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.12% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.93% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.56% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 90.92% 95.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.85% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.33% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 85.09% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.00% 99.23%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.32% 92.94%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.25% 94.00%
CHEMBL221 P23219 Cyclooxygenase-1 83.84% 90.17%
CHEMBL3401 O75469 Pregnane X receptor 83.33% 94.73%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.21% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.12% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.72% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.67% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 80.05% 96.09%

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.
Aspilia foliosa

Cross-Links

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PubChem 162969420
LOTUS LTS0253284
wikiData Q105125371