[(3aR,5S,6E,10Z,11aR)-5-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl acetate

Details

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Internal ID f3e6e93b-1771-4c27-bd0a-0506cf1f0119
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,5S,6E,10Z,11aR)-5-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl acetate
SMILES (Canonical) CC1=CCCC(=CC2C(CC1O)C(=C)C(=O)O2)COC(=O)C
SMILES (Isomeric) C/C/1=C\CC/C(=C/[C@@H]2[C@H](C[C@@H]1O)C(=C)C(=O)O2)/COC(=O)C
InChI InChI=1S/C17H22O5/c1-10-5-4-6-13(9-21-12(3)18)7-16-14(8-15(10)19)11(2)17(20)22-16/h5,7,14-16,19H,2,4,6,8-9H2,1,3H3/b10-5+,13-7-/t14-,15+,16-/m1/s1
InChI Key VJBRGGBTYOAPFB-VBRYBTASSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C17H22O5
Molecular Weight 306.40 g/mol
Exact Mass 306.14672380 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 1.00
Atomic LogP (AlogP) 2.06
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,5S,6E,10Z,11aR)-5-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-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 + 0.9781 97.81%
Caco-2 + 0.5191 51.91%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.7801 78.01%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8832 88.32%
OATP1B3 inhibitior + 0.9531 95.31%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior - 0.5393 53.93%
P-glycoprotein inhibitior - 0.7337 73.37%
P-glycoprotein substrate - 0.8258 82.58%
CYP3A4 substrate + 0.6095 60.95%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8823 88.23%
CYP3A4 inhibition - 0.5572 55.72%
CYP2C9 inhibition - 0.8734 87.34%
CYP2C19 inhibition - 0.8594 85.94%
CYP2D6 inhibition - 0.8762 87.62%
CYP1A2 inhibition - 0.5278 52.78%
CYP2C8 inhibition - 0.5601 56.01%
CYP inhibitory promiscuity - 0.8796 87.96%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7414 74.14%
Eye corrosion - 0.9740 97.40%
Eye irritation - 0.8820 88.20%
Skin irritation - 0.5736 57.36%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7390 73.90%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.6500 65.00%
skin sensitisation - 0.7893 78.93%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.6444 64.44%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.4498 44.98%
Acute Oral Toxicity (c) III 0.6082 60.82%
Estrogen receptor binding - 0.4754 47.54%
Androgen receptor binding - 0.6424 64.24%
Thyroid receptor binding - 0.6573 65.73%
Glucocorticoid receptor binding + 0.7430 74.30%
Aromatase binding - 0.6803 68.03%
PPAR gamma - 0.5631 56.31%
Honey bee toxicity - 0.7958 79.58%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9789 97.89%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.94% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.54% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.29% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.70% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.17% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.95% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.16% 95.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.66% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.97% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.25% 89.00%
CHEMBL2581 P07339 Cathepsin D 83.02% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.73% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.25% 99.23%

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.
Perymenium berlandieri

Cross-Links

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PubChem 162987321
LOTUS LTS0038684
wikiData Q105287149