[(4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-4-methylidene-8-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-4a-yl]methyl acetate

Details

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Internal ID 87e6af92-3f4e-4246-842f-57a5c0e92fdc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name [(4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-4-methylidene-8-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-4a-yl]methyl acetate
SMILES (Canonical) CC1CC(C2(C(C1(C)CCC3=CC(=O)OC3)CCCC2=C)COC(=O)C)OC(=O)C
SMILES (Isomeric) C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)CCC3=CC(=O)OC3)CCCC2=C)COC(=O)C)OC(=O)C
InChI InChI=1S/C24H34O6/c1-15-7-6-8-20-23(5,10-9-19-12-22(27)28-13-19)16(2)11-21(30-18(4)26)24(15,20)14-29-17(3)25/h12,16,20-21H,1,6-11,13-14H2,2-5H3/t16-,20-,21+,23+,24+/m1/s1
InChI Key OMOQXHPINAOUKL-PJYLTOCGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H34O6
Molecular Weight 418.50 g/mol
Exact Mass 418.23553880 g/mol
Topological Polar Surface Area (TPSA) 78.90 Ų
XlogP 3.90
Atomic LogP (AlogP) 4.13
H-Bond Acceptor 6
H-Bond Donor 0
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-4-methylidene-8-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-4a-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9874 98.74%
Caco-2 - 0.5643 56.43%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7247 72.47%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8032 80.32%
OATP1B3 inhibitior + 0.8848 88.48%
MATE1 inhibitior - 0.7000 70.00%
OCT2 inhibitior + 0.5250 52.50%
BSEP inhibitior + 0.7190 71.90%
P-glycoprotein inhibitior + 0.7131 71.31%
P-glycoprotein substrate - 0.5279 52.79%
CYP3A4 substrate + 0.6804 68.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9122 91.22%
CYP3A4 inhibition - 0.7063 70.63%
CYP2C9 inhibition - 0.8283 82.83%
CYP2C19 inhibition - 0.7200 72.00%
CYP2D6 inhibition - 0.9462 94.62%
CYP1A2 inhibition - 0.6955 69.55%
CYP2C8 inhibition + 0.6503 65.03%
CYP inhibitory promiscuity - 0.7665 76.65%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5744 57.44%
Eye corrosion - 0.9846 98.46%
Eye irritation - 0.7995 79.95%
Skin irritation - 0.5312 53.12%
Skin corrosion - 0.9317 93.17%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7306 73.06%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.5162 51.62%
skin sensitisation - 0.8422 84.22%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.4803 48.03%
Acute Oral Toxicity (c) III 0.6340 63.40%
Estrogen receptor binding + 0.8155 81.55%
Androgen receptor binding + 0.5999 59.99%
Thyroid receptor binding + 0.5148 51.48%
Glucocorticoid receptor binding + 0.8042 80.42%
Aromatase binding + 0.7236 72.36%
PPAR gamma + 0.6934 69.34%
Honey bee toxicity - 0.7504 75.04%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5132 51.32%
Fish aquatic toxicity + 1.0000 100.00%

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 97.92% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.63% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.48% 96.09%
CHEMBL2581 P07339 Cathepsin D 93.16% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.17% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.11% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.29% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.55% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.75% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.98% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 85.93% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.57% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.30% 99.23%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.82% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.31% 93.04%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.51% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.05% 95.89%

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.
Ajuga parviflora

Cross-Links

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PubChem 102247112
LOTUS LTS0256461
wikiData Q105194436