[(4S,6R,6aS,9R,10S,10aR)-6-acetyloxy-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-5,7,8,10-tetrahydro-4H-benzo[h][1]benzofuran-4-yl] acetate

Details

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Internal ID e53e992e-e67c-4ffb-bdd3-01f0ebd7fca2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Cadinanolides
IUPAC Name [(4S,6R,6aS,9R,10S,10aR)-6-acetyloxy-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-5,7,8,10-tetrahydro-4H-benzo[h][1]benzofuran-4-yl] acetate
SMILES (Canonical) CC(=O)OC1CC(C2(CCC(C(C23C1=C(C(=O)O3)COC)O)(C)O)O)(C)OC(=O)C
SMILES (Isomeric) CC(=O)O[C@H]1C[C@@]([C@]2(CC[C@@]([C@@H]([C@]23C1=C(C(=O)O3)COC)O)(C)O)O)(C)OC(=O)C
InChI InChI=1S/C20H28O10/c1-10(21)28-13-8-18(4,29-11(2)22)19(26)7-6-17(3,25)16(24)20(19)14(13)12(9-27-5)15(23)30-20/h13,16,24-26H,6-9H2,1-5H3/t13-,16-,17+,18+,19-,20+/m0/s1
InChI Key UHAQFLNYQMGHEC-HCWJOOGXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H28O10
Molecular Weight 428.40 g/mol
Exact Mass 428.16824709 g/mol
Topological Polar Surface Area (TPSA) 149.00 Ų
XlogP -2.10
Atomic LogP (AlogP) -0.48
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4S,6R,6aS,9R,10S,10aR)-6-acetyloxy-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-5,7,8,10-tetrahydro-4H-benzo[h][1]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 + 0.9568 95.68%
Caco-2 - 0.5602 56.02%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8076 80.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8796 87.96%
OATP1B3 inhibitior + 0.9494 94.94%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6345 63.45%
BSEP inhibitior - 0.6613 66.13%
P-glycoprotein inhibitior - 0.6495 64.95%
P-glycoprotein substrate - 0.5232 52.32%
CYP3A4 substrate + 0.7028 70.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8896 88.96%
CYP3A4 inhibition - 0.6741 67.41%
CYP2C9 inhibition - 0.8037 80.37%
CYP2C19 inhibition - 0.8796 87.96%
CYP2D6 inhibition - 0.9399 93.99%
CYP1A2 inhibition - 0.8553 85.53%
CYP2C8 inhibition - 0.5778 57.78%
CYP inhibitory promiscuity - 0.9526 95.26%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5365 53.65%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.8484 84.84%
Skin irritation + 0.5199 51.99%
Skin corrosion - 0.9403 94.03%
Ames mutagenesis + 0.5663 56.63%
Human Ether-a-go-go-Related Gene inhibition - 0.6208 62.08%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.5257 52.57%
skin sensitisation - 0.9109 91.09%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.6508 65.08%
Acute Oral Toxicity (c) III 0.3704 37.04%
Estrogen receptor binding + 0.8108 81.08%
Androgen receptor binding + 0.7233 72.33%
Thyroid receptor binding + 0.5666 56.66%
Glucocorticoid receptor binding + 0.6941 69.41%
Aromatase binding + 0.6684 66.84%
PPAR gamma + 0.6006 60.06%
Honey bee toxicity - 0.7100 71.00%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9759 97.59%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.87% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.10% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.06% 85.14%
CHEMBL2581 P07339 Cathepsin D 96.51% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.34% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.96% 86.33%
CHEMBL226 P30542 Adenosine A1 receptor 90.67% 95.93%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.71% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.52% 89.00%
CHEMBL4208 P20618 Proteasome component C5 85.05% 90.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.95% 82.69%
CHEMBL2996 Q05655 Protein kinase C delta 82.64% 97.79%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.95% 96.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.42% 94.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.25% 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.
Pseudelephantopus spicatus

Cross-Links

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PubChem 162949336
LOTUS LTS0236278
wikiData Q105272685