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(3aS,5aR,6R,9aS,9bS)-5a-methyl-3,9-dimethylidene-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

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 4532706b-5b91-453d-aa74-573089aa1298
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (3aS,5aR,6R,9aS,9bS)-5a-methyl-3,9-dimethylidene-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
SMILES (Canonical) CC12CCC3C(C1C(=C)CCC2OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C3=C
SMILES (Isomeric) C[C@@]12CC[C@@H]3[C@@H]([C@H]1C(=C)CC[C@H]2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)C3=C
InChI InChI=1S/C21H30O8/c1-9-4-5-13(28-20-17(25)16(24)15(23)12(8-22)27-20)21(3)7-6-11-10(2)19(26)29-18(11)14(9)21/h11-18,20,22-25H,1-2,4-8H2,3H3/t11-,12+,13+,14+,15+,16-,17+,18-,20-,21-/m0/s1
InChI Key QSICJOYMTYAQST-FODMJVDISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H30O8
Molecular Weight 410.50 g/mol
Exact Mass 410.19406791 g/mol
Topological Polar Surface Area (TPSA) 126.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 0.04
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3aS,5aR,6R,9aS,9bS)-5a-methyl-3,9-dimethylidene-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7990 79.90%
Caco-2 - 0.7266 72.66%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8072 80.72%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8227 82.27%
OATP1B3 inhibitior + 0.9152 91.52%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior - 0.8191 81.91%
P-glycoprotein inhibitior - 0.7802 78.02%
P-glycoprotein substrate - 0.8933 89.33%
CYP3A4 substrate + 0.6809 68.09%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8749 87.49%
CYP3A4 inhibition - 0.9256 92.56%
CYP2C9 inhibition - 0.8897 88.97%
CYP2C19 inhibition - 0.8798 87.98%
CYP2D6 inhibition - 0.9251 92.51%
CYP1A2 inhibition - 0.8292 82.92%
CYP2C8 inhibition - 0.5568 55.68%
CYP inhibitory promiscuity - 0.8632 86.32%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6291 62.91%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9615 96.15%
Skin irritation - 0.5303 53.03%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis - 0.6870 68.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7668 76.68%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.7674 76.74%
skin sensitisation - 0.8933 89.33%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.5078 50.78%
Acute Oral Toxicity (c) III 0.4202 42.02%
Estrogen receptor binding + 0.6702 67.02%
Androgen receptor binding + 0.6833 68.33%
Thyroid receptor binding + 0.5518 55.18%
Glucocorticoid receptor binding - 0.4854 48.54%
Aromatase binding + 0.6529 65.29%
PPAR gamma + 0.5232 52.32%
Honey bee toxicity - 0.7592 75.92%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9797 97.97%

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 97.22% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.24% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.09% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.96% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.65% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.39% 100.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.35% 95.83%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.27% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.44% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.94% 99.23%
CHEMBL226 P30542 Adenosine A1 receptor 82.07% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 81.97% 96.09%
CHEMBL5255 O00206 Toll-like receptor 4 81.67% 92.50%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.09% 86.92%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.06% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.94% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.86% 92.62%
CHEMBL5555 O00767 Acyl-CoA desaturase 80.58% 97.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.12% 94.00%

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.
Sonchus asper
Sonchus oleraceus

Cross-Links

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PubChem 13855752
LOTUS LTS0227630
wikiData Q105227015