(8-Acetyloxy-9-hydroxy-3,9-dimethyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-3-yl) 2-methylbut-2-enoate

Details

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Internal ID e44b5cdc-d483-419b-a7e3-fbd83d57d15e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (8-acetyloxy-9-hydroxy-3,9-dimethyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-3-yl) 2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1(C2CCC(=C)C3CC(C(C3C2OC1=O)(C)O)OC(=O)C)C
SMILES (Isomeric) CC=C(C)C(=O)OC1(C2CCC(=C)C3CC(C(C3C2OC1=O)(C)O)OC(=O)C)C
InChI InChI=1S/C22H30O7/c1-7-11(2)19(24)29-22(6)15-9-8-12(3)14-10-16(27-13(4)23)21(5,26)17(14)18(15)28-20(22)25/h7,14-18,26H,3,8-10H2,1-2,4-6H3
InChI Key BUYBSZYTQJHXLX-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O7
Molecular Weight 406.50 g/mol
Exact Mass 406.19915329 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.46
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (8-Acetyloxy-9-hydroxy-3,9-dimethyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-3-yl) 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 + 0.9679 96.79%
Caco-2 - 0.5939 59.39%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7209 72.09%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8343 83.43%
OATP1B3 inhibitior + 0.8148 81.48%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6342 63.42%
BSEP inhibitior + 0.7479 74.79%
P-glycoprotein inhibitior + 0.6240 62.40%
P-glycoprotein substrate - 0.6988 69.88%
CYP3A4 substrate + 0.7059 70.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9095 90.95%
CYP3A4 inhibition - 0.7514 75.14%
CYP2C9 inhibition - 0.6788 67.88%
CYP2C19 inhibition - 0.6038 60.38%
CYP2D6 inhibition - 0.9487 94.87%
CYP1A2 inhibition + 0.7050 70.50%
CYP2C8 inhibition + 0.4760 47.60%
CYP inhibitory promiscuity - 0.9537 95.37%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6016 60.16%
Eye corrosion - 0.9778 97.78%
Eye irritation - 0.9231 92.31%
Skin irritation - 0.5156 51.56%
Skin corrosion - 0.9009 90.09%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5826 58.26%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.6836 68.36%
skin sensitisation - 0.8106 81.06%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.5885 58.85%
Acute Oral Toxicity (c) II 0.3621 36.21%
Estrogen receptor binding + 0.8458 84.58%
Androgen receptor binding + 0.6257 62.57%
Thyroid receptor binding + 0.5382 53.82%
Glucocorticoid receptor binding + 0.7322 73.22%
Aromatase binding + 0.6363 63.63%
PPAR gamma + 0.5772 57.72%
Honey bee toxicity - 0.6670 66.70%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9839 98.39%

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 95.22% 91.11%
CHEMBL241 Q14432 Phosphodiesterase 3A 95.20% 92.94%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.90% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 91.95% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.10% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.68% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.18% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.63% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.54% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.36% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.36% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.24% 86.33%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.49% 89.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.02% 92.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.90% 97.14%

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 73172912
LOTUS LTS0203017
wikiData Q104946391