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

Details

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Internal ID 7300d300-7dcd-4b2d-a032-505adb986c93
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name 3-[2-[(1S,2R,4aR,8aR)-1-hydroxy-2,5,5,8a-tetramethyl-3-oxo-2,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
SMILES (Canonical) CC1C(=O)CC2C(CCCC2(C1(CCC3=CC(=O)OC3)O)C)(C)C
SMILES (Isomeric) C[C@H]1C(=O)C[C@H]2[C@]([C@@]1(CCC3=CC(=O)OC3)O)(CCCC2(C)C)C
InChI InChI=1S/C20H30O4/c1-13-15(21)11-16-18(2,3)7-5-8-19(16,4)20(13,23)9-6-14-10-17(22)24-12-14/h10,13,16,23H,5-9,11-12H2,1-4H3/t13-,16+,19+,20-/m0/s1
InChI Key WQXSVWJEQLFYJT-DFXFOWLGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H30O4
Molecular Weight 334.40 g/mol
Exact Mass 334.21440943 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.42
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[2-[(1S,2R,4aR,8aR)-1-hydroxy-2,5,5,8a-tetramethyl-3-oxo-2,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9924 99.24%
Caco-2 + 0.7056 70.56%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.8538 85.38%
OATP2B1 inhibitior - 0.8621 86.21%
OATP1B1 inhibitior + 0.8479 84.79%
OATP1B3 inhibitior + 0.9386 93.86%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior + 0.5287 52.87%
BSEP inhibitior + 0.8659 86.59%
P-glycoprotein inhibitior - 0.6610 66.10%
P-glycoprotein substrate - 0.6670 66.70%
CYP3A4 substrate + 0.5909 59.09%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9148 91.48%
CYP3A4 inhibition - 0.6821 68.21%
CYP2C9 inhibition - 0.7486 74.86%
CYP2C19 inhibition - 0.8823 88.23%
CYP2D6 inhibition - 0.9567 95.67%
CYP1A2 inhibition - 0.8735 87.35%
CYP2C8 inhibition - 0.6277 62.77%
CYP inhibitory promiscuity - 0.9013 90.13%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5727 57.27%
Eye corrosion - 0.9919 99.19%
Eye irritation - 0.8080 80.80%
Skin irritation + 0.5879 58.79%
Skin corrosion - 0.9359 93.59%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4687 46.87%
Micronuclear - 0.8200 82.00%
Hepatotoxicity + 0.6430 64.30%
skin sensitisation - 0.8488 84.88%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.7106 71.06%
Acute Oral Toxicity (c) III 0.4625 46.25%
Estrogen receptor binding + 0.7200 72.00%
Androgen receptor binding + 0.7150 71.50%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7459 74.59%
Aromatase binding + 0.6245 62.45%
PPAR gamma + 0.6572 65.72%
Honey bee toxicity - 0.8593 85.93%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9942 99.42%

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 97.80% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.66% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.00% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.34% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.79% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.70% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.54% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.63% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.03% 97.09%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 83.08% 86.00%
CHEMBL226 P30542 Adenosine A1 receptor 82.65% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.39% 89.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.73% 82.69%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.56% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.37% 93.04%

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.
Leonurus persicus

Cross-Links

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PubChem 162925276
LOTUS LTS0161127
wikiData Q105311050