(2S)-3-[2-[(4S,4aS,8aS)-4-hydroxy-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Details

Top
Internal ID 604708d6-96bb-4b3f-8ef1-3b96d2321392
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (2S)-3-[2-[(4S,4aS,8aS)-4-hydroxy-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
SMILES (Canonical) CC1=C(C2(CCCC(C2C(C1=O)O)(C)C)C)CCC3=CC(=O)OC3O
SMILES (Isomeric) CC1=C([C@]2(CCCC([C@@H]2[C@@H](C1=O)O)(C)C)C)CCC3=CC(=O)O[C@@H]3O
InChI InChI=1S/C20H28O5/c1-11-13(7-6-12-10-14(21)25-18(12)24)20(4)9-5-8-19(2,3)17(20)16(23)15(11)22/h10,16-18,23-24H,5-9H2,1-4H3/t16-,17+,18+,20-/m1/s1
InChI Key XMFSQKSJFSGAHJ-DOADOZAASA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C20H28O5
Molecular Weight 348.40 g/mol
Exact Mass 348.19367399 g/mol
Topological Polar Surface Area (TPSA) 83.80 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.66
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (2S)-3-[2-[(4S,4aS,8aS)-4-hydroxy-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9824 98.24%
Caco-2 + 0.5072 50.72%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7744 77.44%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8401 84.01%
OATP1B3 inhibitior - 0.2629 26.29%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5282 52.82%
BSEP inhibitior + 0.8764 87.64%
P-glycoprotein inhibitior - 0.6595 65.95%
P-glycoprotein substrate - 0.7986 79.86%
CYP3A4 substrate + 0.5896 58.96%
CYP2C9 substrate - 0.7979 79.79%
CYP2D6 substrate - 0.8888 88.88%
CYP3A4 inhibition - 0.6277 62.77%
CYP2C9 inhibition - 0.7006 70.06%
CYP2C19 inhibition - 0.7738 77.38%
CYP2D6 inhibition - 0.9299 92.99%
CYP1A2 inhibition - 0.6520 65.20%
CYP2C8 inhibition - 0.7991 79.91%
CYP inhibitory promiscuity - 0.7504 75.04%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5248 52.48%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.8779 87.79%
Skin irritation + 0.5839 58.39%
Skin corrosion - 0.9230 92.30%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5165 51.65%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.6355 63.55%
skin sensitisation - 0.7233 72.33%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.6231 62.31%
Acute Oral Toxicity (c) I 0.4694 46.94%
Estrogen receptor binding + 0.8200 82.00%
Androgen receptor binding + 0.6147 61.47%
Thyroid receptor binding + 0.5930 59.30%
Glucocorticoid receptor binding + 0.8606 86.06%
Aromatase binding + 0.7220 72.20%
PPAR gamma + 0.7962 79.62%
Honey bee toxicity - 0.8821 88.21%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.86% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.51% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.19% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.09% 97.09%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 87.99% 86.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.43% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.30% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 85.52% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.40% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.88% 94.45%
CHEMBL2581 P07339 Cathepsin D 83.07% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.69% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.05% 89.00%
CHEMBL230 P35354 Cyclooxygenase-2 81.77% 89.63%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.40% 94.00%
CHEMBL1937 Q92769 Histone deacetylase 2 80.37% 94.75%

Plants that contains it

Top
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.
Leonurus sibiricus

Cross-Links

Top
PubChem 163025530
LOTUS LTS0171464
wikiData Q105330713