[(3aS,4R,6E,10R,11aR)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-(acetyloxymethyl)but-2-enoate

Details

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Internal ID 2ad18dc6-d500-48cb-b5f5-7b5107661d8f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4R,6E,10R,11aR)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-(acetyloxymethyl)but-2-enoate
SMILES (Canonical) CC=C(COC(=O)C)C(=O)OC1CC(=CCC(=O)C(CC2C1C(=C)C(=O)O2)C)C
SMILES (Isomeric) C/C=C(\COC(=O)C)/C(=O)O[C@@H]1C/C(=C/CC(=O)[C@@H](C[C@@H]2[C@@H]1C(=C)C(=O)O2)C)/C
InChI InChI=1S/C22H28O7/c1-6-16(11-27-15(5)23)22(26)29-18-9-12(2)7-8-17(24)13(3)10-19-20(18)14(4)21(25)28-19/h6-7,13,18-20H,4,8-11H2,1-3,5H3/b12-7+,16-6+/t13-,18-,19-,20-/m1/s1
InChI Key GVIYUTYDPXUPLJ-IGOIGWPZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O7
Molecular Weight 404.50 g/mol
Exact Mass 404.18350323 g/mol
Topological Polar Surface Area (TPSA) 96.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.84
H-Bond Acceptor 7
H-Bond Donor 0
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4R,6E,10R,11aR)-6,10-dimethyl-3-methylidene-2,9-dioxo-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-(acetyloxymethyl)but-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 + 0.9938 99.38%
Caco-2 + 0.4886 48.86%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6535 65.35%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8682 86.82%
OATP1B3 inhibitior + 0.9168 91.68%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9139 91.39%
P-glycoprotein inhibitior + 0.8248 82.48%
P-glycoprotein substrate - 0.5988 59.88%
CYP3A4 substrate + 0.6474 64.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9057 90.57%
CYP3A4 inhibition - 0.7420 74.20%
CYP2C9 inhibition - 0.8316 83.16%
CYP2C19 inhibition - 0.7597 75.97%
CYP2D6 inhibition - 0.9443 94.43%
CYP1A2 inhibition + 0.5182 51.82%
CYP2C8 inhibition - 0.6027 60.27%
CYP inhibitory promiscuity - 0.8043 80.43%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.6566 65.66%
Eye corrosion - 0.9460 94.60%
Eye irritation - 0.8441 84.41%
Skin irritation - 0.6293 62.93%
Skin corrosion - 0.9550 95.50%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4594 45.94%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.7793 77.93%
skin sensitisation - 0.7305 73.05%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.5222 52.22%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity + 0.7910 79.10%
Acute Oral Toxicity (c) III 0.4887 48.87%
Estrogen receptor binding + 0.6062 60.62%
Androgen receptor binding + 0.6383 63.83%
Thyroid receptor binding - 0.5271 52.71%
Glucocorticoid receptor binding + 0.8266 82.66%
Aromatase binding + 0.5264 52.64%
PPAR gamma - 0.5162 51.62%
Honey bee toxicity - 0.7043 70.43%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9960 99.60%

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 96.11% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.72% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.75% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.17% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 91.09% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.55% 94.45%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 90.22% 97.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.27% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.83% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.70% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.90% 99.23%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.09% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.82% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.09% 89.00%
CHEMBL5028 O14672 ADAM10 80.85% 97.50%
CHEMBL2996 Q05655 Protein kinase C delta 80.44% 97.79%

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.
Stevia jujuyensis

Cross-Links

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PubChem 162992111
LOTUS LTS0275726
wikiData Q105021243