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

Details

Top
Internal ID 54e31fa9-7025-4962-b53e-2ea53016fac5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4R,6Z,9S,10E,11aR)-9-acetyloxy-6-(hydroxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
SMILES (Canonical) CC1=CC2C(C(CC(=CCC1OC(=O)C)CO)OC(=O)C(=CCO)C)C(=C)C(=O)O2
SMILES (Isomeric) C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/C[C@@H]1OC(=O)C)/CO)OC(=O)/C(=C/CO)/C)C(=C)C(=O)O2
InChI InChI=1S/C22H28O8/c1-12(7-8-23)21(26)29-19-10-16(11-24)5-6-17(28-15(4)25)13(2)9-18-20(19)14(3)22(27)30-18/h5,7,9,17-20,23-24H,3,6,8,10-11H2,1-2,4H3/b12-7+,13-9+,16-5-/t17-,18+,19+,20-/m0/s1
InChI Key INXZZSZBRLXKNT-YTLIWXSPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H28O8
Molecular Weight 420.50 g/mol
Exact Mass 420.17841785 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 1.53
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(3aR,4R,6Z,9S,10E,11aR)-9-acetyloxy-6-(hydroxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9450 94.50%
Caco-2 - 0.5973 59.73%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7197 71.97%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8682 86.82%
OATP1B3 inhibitior + 0.9494 94.94%
MATE1 inhibitior - 0.8212 82.12%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8272 82.72%
P-glycoprotein inhibitior + 0.6683 66.83%
P-glycoprotein substrate - 0.6023 60.23%
CYP3A4 substrate + 0.6464 64.64%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9071 90.71%
CYP3A4 inhibition - 0.5918 59.18%
CYP2C9 inhibition - 0.8407 84.07%
CYP2C19 inhibition - 0.8066 80.66%
CYP2D6 inhibition - 0.9337 93.37%
CYP1A2 inhibition - 0.6634 66.34%
CYP2C8 inhibition - 0.5720 57.20%
CYP inhibitory promiscuity - 0.8267 82.67%
UGT catelyzed - 0.6638 66.38%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6282 62.82%
Eye corrosion - 0.9777 97.77%
Eye irritation - 0.9101 91.01%
Skin irritation - 0.6884 68.84%
Skin corrosion - 0.9329 93.29%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3636 36.36%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5032 50.32%
skin sensitisation - 0.8374 83.74%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.5752 57.52%
Acute Oral Toxicity (c) III 0.4777 47.77%
Estrogen receptor binding + 0.7879 78.79%
Androgen receptor binding - 0.5523 55.23%
Thyroid receptor binding - 0.5348 53.48%
Glucocorticoid receptor binding + 0.7788 77.88%
Aromatase binding - 0.5645 56.45%
PPAR gamma + 0.5529 55.29%
Honey bee toxicity - 0.6809 68.09%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9628 96.28%

Targets

Top

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 97.16% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.18% 94.45%
CHEMBL2581 P07339 Cathepsin D 90.69% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 88.24% 94.73%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.49% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.16% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.15% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.14% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.83% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.73% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.31% 93.56%

Plants that contains it

Top
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 breviaristata

Cross-Links

Top
PubChem 87056934
LOTUS LTS0043380
wikiData Q105116480