[(3aS,4R,5Z,8S,9Z,11R,11aR)-8,11-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate

Details

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Internal ID 3a24ced9-2258-4f04-a139-e61fce070f5c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4R,5Z,8S,9Z,11R,11aR)-8,11-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C=C(CC(C=C(C(C2C1C(=C)C(=O)O2)O)C)O)C
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@@H]1/C=C(\C[C@@H](/C=C(\[C@H]([C@H]2[C@H]1C(=C)C(=O)O2)O)/C)O)/C
InChI InChI=1S/C20H28O6/c1-6-11(3)19(23)25-15-8-10(2)7-14(21)9-12(4)17(22)18-16(15)13(5)20(24)26-18/h8-9,11,14-18,21-22H,5-7H2,1-4H3/b10-8-,12-9-/t11-,14+,15-,16+,17-,18-/m1/s1
InChI Key YFXZVQIPUJONOJ-YPGUEBOASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H28O6
Molecular Weight 364.40 g/mol
Exact Mass 364.18858861 g/mol
Topological Polar Surface Area (TPSA) 93.10 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.06
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4R,5Z,8S,9Z,11R,11aR)-8,11-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-4-yl] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9802 98.02%
Caco-2 + 0.5084 50.84%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.4747 47.47%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8526 85.26%
OATP1B3 inhibitior + 0.9072 90.72%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5946 59.46%
P-glycoprotein inhibitior - 0.6538 65.38%
P-glycoprotein substrate - 0.6865 68.65%
CYP3A4 substrate + 0.5947 59.47%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8823 88.23%
CYP3A4 inhibition - 0.6046 60.46%
CYP2C9 inhibition - 0.8304 83.04%
CYP2C19 inhibition - 0.7484 74.84%
CYP2D6 inhibition - 0.9435 94.35%
CYP1A2 inhibition - 0.7790 77.90%
CYP2C8 inhibition - 0.7352 73.52%
CYP inhibitory promiscuity - 0.8695 86.95%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4693 46.93%
Eye corrosion - 0.9704 97.04%
Eye irritation - 0.8993 89.93%
Skin irritation - 0.6171 61.71%
Skin corrosion - 0.9262 92.62%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5475 54.75%
Micronuclear - 0.5700 57.00%
Hepatotoxicity + 0.6486 64.86%
skin sensitisation - 0.7004 70.04%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.6700 67.00%
Acute Oral Toxicity (c) III 0.4381 43.81%
Estrogen receptor binding + 0.6622 66.22%
Androgen receptor binding - 0.5300 53.00%
Thyroid receptor binding - 0.5326 53.26%
Glucocorticoid receptor binding + 0.6109 61.09%
Aromatase binding - 0.5963 59.63%
PPAR gamma - 0.5246 52.46%
Honey bee toxicity - 0.7748 77.48%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6950 69.50%
Fish aquatic toxicity + 0.9440 94.40%

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 93.21% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.15% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.75% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.98% 94.45%
CHEMBL2996 Q05655 Protein kinase C delta 89.33% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 85.76% 90.17%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 85.46% 93.65%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.78% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.71% 86.33%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 84.58% 96.47%
CHEMBL3401 O75469 Pregnane X receptor 84.33% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.22% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.74% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.51% 93.56%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.51% 95.56%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.18% 97.21%

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.
Vicoa indica

Cross-Links

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PubChem 162908012
LOTUS LTS0262855
wikiData Q105347901