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[(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (3R)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate

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 baa29946-9609-4f3a-b788-e43f41b48640
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (3R)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate
SMILES (Canonical) CC(=O)OCC(C(=C)C(=O)OC1CC2(C(CCC(C2C3C1C(=C)C(=O)O3)C=O)O)C)O
SMILES (Isomeric) CC(=O)OC[C@@H](C(=C)C(=O)O[C@H]1C[C@]2([C@@H](CC[C@@H]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C=O)O)C)O
InChI InChI=1S/C22H28O9/c1-10(14(25)9-29-12(3)24)20(27)30-15-7-22(4)16(26)6-5-13(8-23)18(22)19-17(15)11(2)21(28)31-19/h8,13-19,25-26H,1-2,5-7,9H2,3-4H3/t13-,14+,15+,16-,17-,18-,19+,22+/m1/s1
InChI Key OTNZRRSVYLOHOL-WYOWWESVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H28O9
Molecular Weight 436.50 g/mol
Exact Mass 436.17333247 g/mol
Topological Polar Surface Area (TPSA) 136.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 0.47
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (3R)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9882 98.82%
Caco-2 - 0.7394 73.94%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.8281 82.81%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8454 84.54%
OATP1B3 inhibitior + 0.9582 95.82%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5880 58.80%
BSEP inhibitior - 0.6447 64.47%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5720 57.20%
CYP3A4 substrate + 0.6991 69.91%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8837 88.37%
CYP3A4 inhibition - 0.5767 57.67%
CYP2C9 inhibition - 0.8064 80.64%
CYP2C19 inhibition - 0.9180 91.80%
CYP2D6 inhibition - 0.9410 94.10%
CYP1A2 inhibition - 0.8452 84.52%
CYP2C8 inhibition + 0.4774 47.74%
CYP inhibitory promiscuity - 0.8923 89.23%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5964 59.64%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9151 91.51%
Skin irritation + 0.5785 57.85%
Skin corrosion - 0.9284 92.84%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5087 50.87%
Micronuclear - 0.7700 77.00%
Hepatotoxicity + 0.6255 62.55%
skin sensitisation - 0.8955 89.55%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.7507 75.07%
Acute Oral Toxicity (c) I 0.3119 31.19%
Estrogen receptor binding + 0.8321 83.21%
Androgen receptor binding + 0.6586 65.86%
Thyroid receptor binding + 0.5329 53.29%
Glucocorticoid receptor binding + 0.6703 67.03%
Aromatase binding + 0.5973 59.73%
PPAR gamma + 0.6396 63.96%
Honey bee toxicity - 0.6497 64.97%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9954 99.54%

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 98.90% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.60% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.53% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.37% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 92.92% 90.17%
CHEMBL2581 P07339 Cathepsin D 91.99% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.29% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.97% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.75% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.65% 100.00%
CHEMBL1871 P10275 Androgen Receptor 84.85% 96.43%
CHEMBL1951 P21397 Monoamine oxidase A 84.38% 91.49%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.09% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 83.71% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.38% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.84% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.43% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.27% 95.89%
CHEMBL5028 O14672 ADAM10 81.75% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.23% 91.07%
CHEMBL204 P00734 Thrombin 80.21% 96.01%
CHEMBL3401 O75469 Pregnane X receptor 80.14% 94.73%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.10% 100.00%

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.
Centaurea spinosa

Cross-Links

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PubChem 44566536
LOTUS LTS0023615
wikiData Q105199713