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[(3aR,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID bef47f66-2799-4880-8825-37032ddf73fc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate
SMILES (Canonical) CC1CC2C(C(C(C(C(=O)C=C1)(C)O)OC(=O)C)OC(=O)C(C)C)C(=C)C(=O)O2
SMILES (Isomeric) C[C@@H]/1C[C@@H]2[C@H]([C@@H]([C@H]([C@@](C(=O)/C=C1)(C)O)OC(=O)C)OC(=O)C(C)C)C(=C)C(=O)O2
InChI InChI=1S/C21H28O8/c1-10(2)19(24)29-17-16-12(4)20(25)28-14(16)9-11(3)7-8-15(23)21(6,26)18(17)27-13(5)22/h7-8,10-11,14,16-18,26H,4,9H2,1-3,5-6H3/b8-7-/t11-,14+,16+,17-,18+,21-/m0/s1
InChI Key BGNYEVHTEQZTRS-SZWSCDJLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H28O8
Molecular Weight 408.40 g/mol
Exact Mass 408.17841785 g/mol
Topological Polar Surface Area (TPSA) 116.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.50
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

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 - 0.5125 51.25%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.6429 64.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8566 85.66%
OATP1B3 inhibitior + 0.8407 84.07%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8008 80.08%
P-glycoprotein inhibitior + 0.6655 66.55%
P-glycoprotein substrate - 0.6920 69.20%
CYP3A4 substrate + 0.6439 64.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9150 91.50%
CYP3A4 inhibition - 0.7367 73.67%
CYP2C9 inhibition - 0.8831 88.31%
CYP2C19 inhibition - 0.8676 86.76%
CYP2D6 inhibition - 0.9432 94.32%
CYP1A2 inhibition - 0.8212 82.12%
CYP2C8 inhibition - 0.6540 65.40%
CYP inhibitory promiscuity - 0.9204 92.04%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8843 88.43%
Carcinogenicity (trinary) Non-required 0.4256 42.56%
Eye corrosion - 0.9541 95.41%
Eye irritation - 0.9003 90.03%
Skin irritation - 0.6563 65.63%
Skin corrosion - 0.9131 91.31%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5471 54.71%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.7875 78.75%
skin sensitisation - 0.5334 53.34%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.5222 52.22%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.5794 57.94%
Acute Oral Toxicity (c) III 0.4112 41.12%
Estrogen receptor binding + 0.7850 78.50%
Androgen receptor binding + 0.5869 58.69%
Thyroid receptor binding + 0.5482 54.82%
Glucocorticoid receptor binding + 0.7332 73.32%
Aromatase binding + 0.5368 53.68%
PPAR gamma + 0.7343 73.43%
Honey bee toxicity - 0.6255 62.55%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9558 95.58%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.75% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.82% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.38% 85.14%
CHEMBL2996 Q05655 Protein kinase C delta 93.52% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.15% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.03% 95.56%
CHEMBL299 P17252 Protein kinase C alpha 92.97% 98.03%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.43% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.00% 86.33%
CHEMBL2581 P07339 Cathepsin D 87.92% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.57% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 86.99% 91.19%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.69% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.02% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.71% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.90% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.75% 97.14%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.91% 98.75%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.02% 89.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 82.44% 83.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 80.57% 96.47%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.36% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.32% 94.00%
CHEMBL5028 O14672 ADAM10 80.07% 97.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.00% 100.00%

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.
Neurolaena oaxacana

Cross-Links

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PubChem 162900828
LOTUS LTS0125476
wikiData Q104935655