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[(3aS,6R,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl 3-methylbutanoate

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 1e61796e-b7ae-4567-b1a5-a2c120bcf6c1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
IUPAC Name [(3aS,6R,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylidene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl 3-methylbutanoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C20H28O6/c1-11(2)9-16(22)25-10-13-5-6-14-12(3)18(23)26-17(14)19(4)15(21)7-8-20(13,19)24/h11,13-14,17,24H,3,5-10H2,1-2,4H3/t13-,14+,17-,19+,20-/m1/s1
InChI Key NGKFAMFILMKFJI-DZDZPLTMSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C20H28O6
Molecular Weight 364.40 g/mol
Exact Mass 364.18858861 g/mol
Topological Polar Surface Area (TPSA) 89.90 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.18
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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[(3aS,6R,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl 3-methylbutanoate
Butanoic acid, 3-methyl-, [(3aS,6R,6aR,9aS,9bR)-dodecahydro-6a-hydroxy-9a-methyl-3-methylene-2,9-dioxoazuleno[4,5-b]furan-6-yl]methyl ester

2D Structure

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2D Structure of [(3aS,6R,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl 3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9837 98.37%
Caco-2 + 0.5348 53.48%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.7483 74.83%
OATP2B1 inhibitior - 0.8614 86.14%
OATP1B1 inhibitior + 0.8790 87.90%
OATP1B3 inhibitior + 0.9021 90.21%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.6114 61.14%
BSEP inhibitior - 0.8750 87.50%
P-glycoprotein inhibitior - 0.6290 62.90%
P-glycoprotein substrate - 0.7419 74.19%
CYP3A4 substrate + 0.6533 65.33%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9010 90.10%
CYP3A4 inhibition - 0.5943 59.43%
CYP2C9 inhibition + 0.5779 57.79%
CYP2C19 inhibition - 0.7366 73.66%
CYP2D6 inhibition - 0.9479 94.79%
CYP1A2 inhibition - 0.5260 52.60%
CYP2C8 inhibition - 0.6432 64.32%
CYP inhibitory promiscuity - 0.9147 91.47%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6342 63.42%
Eye corrosion - 0.9843 98.43%
Eye irritation - 0.8772 87.72%
Skin irritation - 0.5158 51.58%
Skin corrosion - 0.9351 93.51%
Ames mutagenesis - 0.7354 73.54%
Human Ether-a-go-go-Related Gene inhibition - 0.6549 65.49%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.5050 50.50%
skin sensitisation - 0.8406 84.06%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.5565 55.65%
Acute Oral Toxicity (c) III 0.3863 38.63%
Estrogen receptor binding + 0.8036 80.36%
Androgen receptor binding + 0.6017 60.17%
Thyroid receptor binding + 0.5130 51.30%
Glucocorticoid receptor binding + 0.7439 74.39%
Aromatase binding + 0.6953 69.53%
PPAR gamma + 0.5774 57.74%
Honey bee toxicity - 0.8786 87.86%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9930 99.30%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.48% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.40% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.68% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.51% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.72% 97.09%
CHEMBL2996 Q05655 Protein kinase C delta 90.49% 97.79%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.83% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 89.00% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.87% 99.23%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.72% 92.62%
CHEMBL2581 P07339 Cathepsin D 85.22% 98.95%
CHEMBL1937 Q92769 Histone deacetylase 2 85.03% 94.75%
CHEMBL299 P17252 Protein kinase C alpha 84.79% 98.03%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.70% 82.69%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.14% 93.04%
CHEMBL5028 O14672 ADAM10 81.65% 97.50%
CHEMBL226 P30542 Adenosine A1 receptor 81.31% 95.93%
CHEMBL1871 P10275 Androgen Receptor 80.93% 96.43%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.92% 86.33%
CHEMBL5957 P21589 5'-nucleotidase 80.84% 97.78%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.40% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.37% 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.
Parthenium hysterophorus

Cross-Links

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PubChem 16729351
LOTUS LTS0259270
wikiData Q105178970