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[(3S,3aR,3bR,4R,5aS,9aS,9bR,11aR)-3-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-3,3a,4,5,5a,7,8,9,9b,10,11,11a-dodecahydronaphtho[2,1-e][2]benzofuran-4-yl] acetate

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 b03f75be-3401-4ad2-801d-36a1909c27b8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name [(3S,3aR,3bR,4R,5aS,9aS,9bR,11aR)-3-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-3,3a,4,5,5a,7,8,9,9b,10,11,11a-dodecahydronaphtho[2,1-e][2]benzofuran-4-yl] acetate
SMILES (Canonical) CC(=O)OC1CC2C(CCCC2(C3C1(C4C(CC3)C(=O)OC4O)C)C)(C)C
SMILES (Isomeric) CC(=O)O[C@@H]1C[C@@H]2[C@](CCCC2(C)C)([C@@H]3[C@@]1([C@H]4[C@@H](CC3)C(=O)O[C@@H]4O)C)C
InChI InChI=1S/C22H34O5/c1-12(23)26-16-11-15-20(2,3)9-6-10-21(15,4)14-8-7-13-17(22(14,16)5)19(25)27-18(13)24/h13-17,19,25H,6-11H2,1-5H3/t13-,14-,15+,16-,17+,19+,21-,22+/m1/s1
InChI Key LECDDGVBLOGBTB-RPXMUJGOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H34O5
Molecular Weight 378.50 g/mol
Exact Mass 378.24062418 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 4.80
Atomic LogP (AlogP) 3.68
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3S,3aR,3bR,4R,5aS,9aS,9bR,11aR)-3-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-3,3a,4,5,5a,7,8,9,9b,10,11,11a-dodecahydronaphtho[2,1-e][2]benzofuran-4-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9711 97.11%
Caco-2 + 0.5410 54.10%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7707 77.07%
OATP2B1 inhibitior - 0.8656 86.56%
OATP1B1 inhibitior + 0.8599 85.99%
OATP1B3 inhibitior + 0.9097 90.97%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.7506 75.06%
P-glycoprotein inhibitior - 0.5664 56.64%
P-glycoprotein substrate - 0.8382 83.82%
CYP3A4 substrate + 0.6588 65.88%
CYP2C9 substrate - 0.8042 80.42%
CYP2D6 substrate - 0.8618 86.18%
CYP3A4 inhibition - 0.7563 75.63%
CYP2C9 inhibition - 0.7647 76.47%
CYP2C19 inhibition - 0.8143 81.43%
CYP2D6 inhibition - 0.9677 96.77%
CYP1A2 inhibition - 0.7801 78.01%
CYP2C8 inhibition - 0.5600 56.00%
CYP inhibitory promiscuity - 0.9559 95.59%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6472 64.72%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9413 94.13%
Skin irritation + 0.4908 49.08%
Skin corrosion - 0.8211 82.11%
Ames mutagenesis - 0.7064 70.64%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8706 87.06%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.5480 54.80%
Acute Oral Toxicity (c) III 0.4582 45.82%
Estrogen receptor binding + 0.8543 85.43%
Androgen receptor binding + 0.5499 54.99%
Thyroid receptor binding + 0.6142 61.42%
Glucocorticoid receptor binding + 0.7022 70.22%
Aromatase binding + 0.6316 63.16%
PPAR gamma + 0.7295 72.95%
Honey bee toxicity - 0.7856 78.56%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9884 98.84%

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 94.50% 91.11%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 93.96% 96.38%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.91% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.81% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.33% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.47% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 88.03% 91.19%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.62% 96.77%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.38% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.95% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.76% 93.04%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.63% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.48% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.96% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.52% 86.33%
CHEMBL2581 P07339 Cathepsin D 82.82% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.36% 95.56%
CHEMBL5255 O00206 Toll-like receptor 4 81.76% 92.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.35% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.26% 99.23%
CHEMBL5028 O14672 ADAM10 80.88% 97.50%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 80.36% 95.58%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.06% 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.
There are no matching plants.

Cross-Links

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PubChem 163045777
LOTUS LTS0114317
wikiData Q105150494