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

Details

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Internal ID 1cc2bd16-ec01-4945-ab39-fa9845152715
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4S,5Z,7S,9S,10Z,11aS)-9-acetyloxy-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C=C(C(CC(C(=CC2C1C(=C)C(=O)O2)CO)OC(=O)C)O)C
SMILES (Isomeric) CC[C@H](C)C(=O)O[C@H]1/C=C(\[C@H](C[C@@H](/C(=C\[C@H]2[C@@H]1C(=C)C(=O)O2)/CO)OC(=O)C)O)/C
InChI InChI=1S/C22H30O8/c1-6-11(2)21(26)29-18-7-12(3)16(25)9-17(28-14(5)24)15(10-23)8-19-20(18)13(4)22(27)30-19/h7-8,11,16-20,23,25H,4,6,9-10H2,1-3,5H3/b12-7-,15-8-/t11-,16-,17-,18-,19-,20+/m0/s1
InChI Key YZCAXCLLBWHFLS-ALLFZCPISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O8
Molecular Weight 422.50 g/mol
Exact Mass 422.19406791 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 0.10
Atomic LogP (AlogP) 1.60
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5Z,7S,9S,10Z,11aS)-9-acetyloxy-7-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S)-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 + 0.9829 98.29%
Caco-2 - 0.6227 62.27%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5582 55.82%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8607 86.07%
OATP1B3 inhibitior + 0.9562 95.62%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.7155 71.55%
P-glycoprotein inhibitior + 0.5817 58.17%
P-glycoprotein substrate - 0.5446 54.46%
CYP3A4 substrate + 0.6292 62.92%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8838 88.38%
CYP3A4 inhibition + 0.6986 69.86%
CYP2C9 inhibition - 0.8227 82.27%
CYP2C19 inhibition - 0.8088 80.88%
CYP2D6 inhibition - 0.9329 93.29%
CYP1A2 inhibition - 0.6232 62.32%
CYP2C8 inhibition - 0.6498 64.98%
CYP inhibitory promiscuity - 0.8207 82.07%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6060 60.60%
Eye corrosion - 0.9829 98.29%
Eye irritation - 0.8679 86.79%
Skin irritation - 0.5654 56.54%
Skin corrosion - 0.9381 93.81%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5818 58.18%
Micronuclear - 0.7700 77.00%
Hepatotoxicity + 0.6963 69.63%
skin sensitisation - 0.8507 85.07%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.7071 70.71%
Acute Oral Toxicity (c) III 0.5491 54.91%
Estrogen receptor binding + 0.8288 82.88%
Androgen receptor binding - 0.5516 55.16%
Thyroid receptor binding - 0.5749 57.49%
Glucocorticoid receptor binding + 0.7976 79.76%
Aromatase binding - 0.5603 56.03%
PPAR gamma - 0.5053 50.53%
Honey bee toxicity - 0.7186 71.86%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity + 0.9816 98.16%

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
CHEMBL2996 Q05655 Protein kinase C delta 96.40% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.56% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.10% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.05% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.39% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.90% 89.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.34% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.67% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.75% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.57% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.38% 95.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.06% 95.50%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.96% 96.47%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.54% 93.56%
CHEMBL3401 O75469 Pregnane X receptor 80.10% 94.73%

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.
Eupatorium mohrii

Cross-Links

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PubChem 162947111
LOTUS LTS0036411
wikiData Q105369123