(4S,4aR,5S,8aR,9aR)-4-methoxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

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Internal ID 8973664e-7b8b-4dbe-884e-408e6daf8e64
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name (4S,4aR,5S,8aR,9aR)-4-methoxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-2-one
SMILES (Canonical) CC1CCCC2C1(C(C3=C(C(=O)OC3C2)C)OC)C
SMILES (Isomeric) C[C@H]1CCC[C@H]2[C@@]1([C@@H](C3=C(C(=O)O[C@@H]3C2)C)OC)C
InChI InChI=1S/C16H24O3/c1-9-6-5-7-11-8-12-13(10(2)15(17)19-12)14(18-4)16(9,11)3/h9,11-12,14H,5-8H2,1-4H3/t9-,11+,12+,14+,16+/m0/s1
InChI Key WCODIXDFMCJVPU-MEJBDBETSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C16H24O3
Molecular Weight 264.36 g/mol
Exact Mass 264.17254462 g/mol
Topological Polar Surface Area (TPSA) 35.50 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.09
H-Bond Acceptor 3
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (4S,4aR,5S,8aR,9aR)-4-methoxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][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 + 0.9970 99.70%
Caco-2 + 0.9480 94.80%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.5887 58.87%
OATP2B1 inhibitior - 0.8522 85.22%
OATP1B1 inhibitior + 0.9008 90.08%
OATP1B3 inhibitior + 0.9790 97.90%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior - 0.8795 87.95%
P-glycoprotein inhibitior - 0.7756 77.56%
P-glycoprotein substrate - 0.8518 85.18%
CYP3A4 substrate + 0.6190 61.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8844 88.44%
CYP3A4 inhibition - 0.7304 73.04%
CYP2C9 inhibition - 0.8303 83.03%
CYP2C19 inhibition - 0.6254 62.54%
CYP2D6 inhibition - 0.9565 95.65%
CYP1A2 inhibition + 0.5264 52.64%
CYP2C8 inhibition - 0.8031 80.31%
CYP inhibitory promiscuity - 0.7780 77.80%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4894 48.94%
Eye corrosion - 0.9855 98.55%
Eye irritation - 0.8131 81.31%
Skin irritation - 0.5475 54.75%
Skin corrosion - 0.9403 94.03%
Ames mutagenesis - 0.6464 64.64%
Human Ether-a-go-go-Related Gene inhibition - 0.4157 41.57%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.7125 71.25%
skin sensitisation - 0.7499 74.99%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.5991 59.91%
Acute Oral Toxicity (c) III 0.4968 49.68%
Estrogen receptor binding + 0.7447 74.47%
Androgen receptor binding + 0.5190 51.90%
Thyroid receptor binding + 0.6107 61.07%
Glucocorticoid receptor binding + 0.6403 64.03%
Aromatase binding - 0.6714 67.14%
PPAR gamma + 0.5242 52.42%
Honey bee toxicity - 0.7812 78.12%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.9887 98.87%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.46% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.50% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.75% 99.23%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.65% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.52% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.76% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.83% 86.33%
CHEMBL1902 P62942 FK506-binding protein 1A 84.78% 97.05%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.10% 92.94%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.33% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.37% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.05% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.04% 93.03%
CHEMBL2581 P07339 Cathepsin D 80.92% 98.95%

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.
Ligularia virgaurea

Cross-Links

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PubChem 163016547
LOTUS LTS0217926
wikiData Q105301911