[(3S,3aR,6S,6aS,9aS,9bS)-6-hydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 9dc21274-e8df-4b59-899c-d430b431b7b8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3S,3aR,6S,6aS,9aS,9bS)-6-hydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1(C2CCC(C3CC=C(C3C2OC1=O)C)(C)O)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@]1([C@@H]2CC[C@]([C@H]3CC=C([C@H]3[C@@H]2OC1=O)C)(C)O)C
InChI InChI=1S/C20H28O5/c1-6-11(2)17(21)25-20(5)14-9-10-19(4,23)13-8-7-12(3)15(13)16(14)24-18(20)22/h6-7,13-16,23H,8-10H2,1-5H3/b11-6-/t13-,14+,15+,16+,19-,20-/m0/s1
InChI Key ZMIXRMAFAZHXRQ-XVYFMLOKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H28O5
Molecular Weight 348.40 g/mol
Exact Mass 348.19367399 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.92
H-Bond Acceptor 5
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 [(3S,3aR,6S,6aS,9aS,9bS)-6-hydroxy-3,6,9-trimethyl-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-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 + 0.9880 98.80%
Caco-2 + 0.5540 55.40%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.6605 66.05%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8881 88.81%
OATP1B3 inhibitior + 0.9044 90.44%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7771 77.71%
BSEP inhibitior - 0.6131 61.31%
P-glycoprotein inhibitior - 0.5334 53.34%
P-glycoprotein substrate - 0.7013 70.13%
CYP3A4 substrate + 0.6684 66.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8914 89.14%
CYP3A4 inhibition - 0.6619 66.19%
CYP2C9 inhibition - 0.6748 67.48%
CYP2C19 inhibition - 0.7167 71.67%
CYP2D6 inhibition - 0.9590 95.90%
CYP1A2 inhibition + 0.6041 60.41%
CYP2C8 inhibition - 0.7476 74.76%
CYP inhibitory promiscuity - 0.9750 97.50%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5754 57.54%
Eye corrosion - 0.9846 98.46%
Eye irritation - 0.9645 96.45%
Skin irritation + 0.5632 56.32%
Skin corrosion - 0.9044 90.44%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6085 60.85%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.6941 69.41%
skin sensitisation - 0.8333 83.33%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.7259 72.59%
Acute Oral Toxicity (c) IV 0.3191 31.91%
Estrogen receptor binding + 0.7798 77.98%
Androgen receptor binding + 0.6038 60.38%
Thyroid receptor binding + 0.6049 60.49%
Glucocorticoid receptor binding + 0.6995 69.95%
Aromatase binding - 0.5310 53.10%
PPAR gamma + 0.5697 56.97%
Honey bee toxicity - 0.7607 76.07%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9727 97.27%

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 93.82% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.47% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.71% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.04% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.81% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.40% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.97% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.62% 100.00%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 86.10% 85.30%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.84% 96.09%
CHEMBL1871 P10275 Androgen Receptor 83.62% 96.43%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.71% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.81% 97.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.25% 92.94%

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.
Thapsia nitida

Cross-Links

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PubChem 23255564
LOTUS LTS0059295
wikiData Q105379475