[(1R,2R,5S,6S,9S,10S,12S,13R)-5,9-dimethyl-14-methylidene-4-oxo-3,11-dioxatetracyclo[7.5.0.02,6.010,12]tetradecan-13-yl] 3-methylbut-2-enoate

Details

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Internal ID a97a964c-ba47-49fc-b81d-e19e8e684e1b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(1R,2R,5S,6S,9S,10S,12S,13R)-5,9-dimethyl-14-methylidene-4-oxo-3,11-dioxatetracyclo[7.5.0.02,6.010,12]tetradecan-13-yl] 3-methylbut-2-enoate
SMILES (Canonical) CC1C2CCC3(C(C2OC1=O)C(=C)C(C4C3O4)OC(=O)C=C(C)C)C
SMILES (Isomeric) C[C@H]1[C@@H]2CC[C@]3([C@H]([C@@H]2OC1=O)C(=C)[C@H]([C@@H]4[C@H]3O4)OC(=O)C=C(C)C)C
InChI InChI=1S/C20H26O5/c1-9(2)8-13(21)23-15-11(4)14-16-12(10(3)19(22)25-16)6-7-20(14,5)18-17(15)24-18/h8,10,12,14-18H,4,6-7H2,1-3,5H3/t10-,12-,14-,15+,16+,17+,18+,20-/m0/s1
InChI Key BLEFUIRCOMJZMD-ZPDBXDRJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O5
Molecular Weight 346.40 g/mol
Exact Mass 346.17802393 g/mol
Topological Polar Surface Area (TPSA) 65.10 Ų
XlogP 3.10
Atomic LogP (AlogP) 2.80
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2R,5S,6S,9S,10S,12S,13R)-5,9-dimethyl-14-methylidene-4-oxo-3,11-dioxatetracyclo[7.5.0.02,6.010,12]tetradecan-13-yl] 3-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9871 98.71%
Caco-2 + 0.6010 60.10%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.6115 61.15%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8723 87.23%
OATP1B3 inhibitior + 0.8916 89.16%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.5984 59.84%
P-glycoprotein inhibitior - 0.4594 45.94%
P-glycoprotein substrate - 0.6389 63.89%
CYP3A4 substrate + 0.7190 71.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9046 90.46%
CYP3A4 inhibition + 0.5000 50.00%
CYP2C9 inhibition - 0.7491 74.91%
CYP2C19 inhibition - 0.7416 74.16%
CYP2D6 inhibition - 0.9060 90.60%
CYP1A2 inhibition - 0.5308 53.08%
CYP2C8 inhibition - 0.7570 75.70%
CYP inhibitory promiscuity - 0.7084 70.84%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.4799 47.99%
Eye corrosion - 0.9829 98.29%
Eye irritation - 0.8147 81.47%
Skin irritation - 0.6074 60.74%
Skin corrosion - 0.8566 85.66%
Ames mutagenesis - 0.6260 62.60%
Human Ether-a-go-go-Related Gene inhibition - 0.6345 63.45%
Micronuclear - 0.6100 61.00%
Hepatotoxicity + 0.6727 67.27%
skin sensitisation - 0.6521 65.21%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.5678 56.78%
Acute Oral Toxicity (c) III 0.5100 51.00%
Estrogen receptor binding + 0.7628 76.28%
Androgen receptor binding + 0.6338 63.38%
Thyroid receptor binding + 0.5321 53.21%
Glucocorticoid receptor binding + 0.7295 72.95%
Aromatase binding + 0.5254 52.54%
PPAR gamma + 0.6537 65.37%
Honey bee toxicity - 0.5838 58.38%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9958 99.58%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.82% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.21% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.66% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.39% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.69% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.97% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.40% 93.04%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.28% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 84.33% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.65% 99.23%
CHEMBL4105786 P41182 B-cell lymphoma 6 protein 83.41% 92.86%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.28% 86.33%
CHEMBL2581 P07339 Cathepsin D 81.67% 98.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.58% 97.14%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.56% 93.03%
CHEMBL1937 Q92769 Histone deacetylase 2 80.56% 94.75%

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.
Thapsia nitida

Cross-Links

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PubChem 11995474
LOTUS LTS0028892
wikiData Q104937937