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[(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (2S,3S)-2,3-dimethyloxirane-2-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 f6916340-afcf-4de4-bd8b-1e0c4f2e75d3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC1C(O1)(C)C(=O)OC2CCC3(CO3)C4C2(CC(C5C4OC(=O)C5=C)O)C
SMILES (Isomeric) C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2CC[C@]3(CO3)[C@H]4[C@]2(C[C@@H]([C@@H]5[C@@H]4OC(=O)C5=C)O)C
InChI InChI=1S/C20H26O7/c1-9-13-11(21)7-18(3)12(25-17(23)19(4)10(2)27-19)5-6-20(8-24-20)15(18)14(13)26-16(9)22/h10-15,21H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14-,15+,18-,19-,20-/m0/s1
InChI Key DBLRZEPMSCXOHA-QUMNMRMJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O7
Molecular Weight 378.40 g/mol
Exact Mass 378.16785316 g/mol
Topological Polar Surface Area (TPSA) 97.90 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.12
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9855 98.55%
Caco-2 + 0.5092 50.92%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7696 76.96%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8810 88.10%
OATP1B3 inhibitior + 0.9420 94.20%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5521 55.21%
BSEP inhibitior - 0.7163 71.63%
P-glycoprotein inhibitior - 0.6215 62.15%
P-glycoprotein substrate - 0.6215 62.15%
CYP3A4 substrate + 0.6912 69.12%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8492 84.92%
CYP3A4 inhibition - 0.5556 55.56%
CYP2C9 inhibition - 0.8009 80.09%
CYP2C19 inhibition - 0.9099 90.99%
CYP2D6 inhibition - 0.9411 94.11%
CYP1A2 inhibition - 0.7667 76.67%
CYP2C8 inhibition - 0.7162 71.62%
CYP inhibitory promiscuity - 0.9545 95.45%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4896 48.96%
Eye corrosion - 0.9876 98.76%
Eye irritation - 0.9408 94.08%
Skin irritation + 0.5516 55.16%
Skin corrosion - 0.9183 91.83%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5347 53.47%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.6639 66.39%
skin sensitisation - 0.8355 83.55%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.8130 81.30%
Acute Oral Toxicity (c) III 0.3577 35.77%
Estrogen receptor binding + 0.8262 82.62%
Androgen receptor binding + 0.6540 65.40%
Thyroid receptor binding + 0.5802 58.02%
Glucocorticoid receptor binding + 0.7423 74.23%
Aromatase binding + 0.6065 60.65%
PPAR gamma + 0.6512 65.12%
Honey bee toxicity - 0.7312 73.12%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5250 52.50%
Fish aquatic toxicity + 0.9924 99.24%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.21% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 97.73% 83.82%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 93.38% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.42% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.85% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.16% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.80% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.78% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.46% 95.56%
CHEMBL218 P21554 Cannabinoid CB1 receptor 87.57% 96.61%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.03% 82.69%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.54% 92.94%
CHEMBL2581 P07339 Cathepsin D 86.38% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.72% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.40% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.19% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.46% 96.09%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.43% 98.75%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.57% 97.28%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.95% 93.03%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.93% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.90% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 80.01% 90.17%

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.
Dimerostemma brasilianum

Cross-Links

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PubChem 162995799
LOTUS LTS0031281
wikiData Q104974536