(3S,3aS,5aR,6S,9R,9aS,9bS)-6,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one

Details

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Internal ID a45924cf-6cff-4fbd-82f2-f765857d0fcd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (3S,3aS,5aR,6S,9R,9aS,9bS)-6,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
SMILES (Canonical) CC1C2CCC3(C(C=CC(C3C2OC1=O)(C)O)O)C
SMILES (Isomeric) C[C@H]1[C@@H]2CC[C@]3([C@H](C=C[C@@]([C@@H]3[C@H]2OC1=O)(C)O)O)C
InChI InChI=1S/C15H22O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-12,16,18H,4,6H2,1-3H3/t8-,9-,10-,11-,12+,14-,15+/m0/s1
InChI Key WKSCGYPNYYBCSB-MVDQFSNNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H22O4
Molecular Weight 266.33 g/mol
Exact Mass 266.15180918 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.26
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,3aS,5aR,6S,9R,9aS,9bS)-6,9-dihydroxy-3,5a,9-trimethyl-3a,4,5,6,9a,9b-hexahydro-3H-benzo[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 + 0.9822 98.22%
Caco-2 - 0.6668 66.68%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability + 0.6000 60.00%
Subcellular localzation Mitochondria 0.5896 58.96%
OATP2B1 inhibitior - 0.8536 85.36%
OATP1B1 inhibitior + 0.9094 90.94%
OATP1B3 inhibitior + 0.9077 90.77%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7071 70.71%
BSEP inhibitior - 0.9345 93.45%
P-glycoprotein inhibitior - 0.9317 93.17%
P-glycoprotein substrate - 0.8295 82.95%
CYP3A4 substrate + 0.6191 61.91%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8629 86.29%
CYP3A4 inhibition - 0.6307 63.07%
CYP2C9 inhibition - 0.8410 84.10%
CYP2C19 inhibition - 0.8808 88.08%
CYP2D6 inhibition - 0.9514 95.14%
CYP1A2 inhibition + 0.5412 54.12%
CYP2C8 inhibition - 0.9499 94.99%
CYP inhibitory promiscuity - 0.7924 79.24%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4403 44.03%
Eye corrosion - 0.9870 98.70%
Eye irritation - 0.9781 97.81%
Skin irritation + 0.5744 57.44%
Skin corrosion - 0.7716 77.16%
Ames mutagenesis - 0.7611 76.11%
Human Ether-a-go-go-Related Gene inhibition - 0.5839 58.39%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.7357 73.57%
skin sensitisation - 0.7546 75.46%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.5784 57.84%
Acute Oral Toxicity (c) III 0.3811 38.11%
Estrogen receptor binding + 0.5482 54.82%
Androgen receptor binding + 0.5457 54.57%
Thyroid receptor binding + 0.5415 54.15%
Glucocorticoid receptor binding + 0.5612 56.12%
Aromatase binding - 0.7916 79.16%
PPAR gamma - 0.6919 69.19%
Honey bee toxicity - 0.8645 86.45%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9791 97.91%

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 93.14% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.97% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.55% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.39% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.32% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.25% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.07% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.43% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.87% 99.23%
CHEMBL2581 P07339 Cathepsin D 81.04% 98.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.72% 93.04%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.71% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.41% 96.77%

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.
Artemisia cana
Seriphidium spicigerum

Cross-Links

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PubChem 101034725
LOTUS LTS0241522
wikiData Q105307662