[(3aS,5aS,7S,9bR)-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-7-yl] acetate

Details

Top
Internal ID 85c4e8b4-9e7c-4180-a50a-0350fb3dcf4a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aS,5aS,7S,9bR)-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-7-yl] acetate
SMILES (Canonical) CC1=C2C3C(CCC2(CC(C1)OC(=O)C)C)C(=C)C(=O)O3
SMILES (Isomeric) CC1=C2[C@H]3[C@@H](CC[C@]2(C[C@H](C1)OC(=O)C)C)C(=C)C(=O)O3
InChI InChI=1S/C17H22O4/c1-9-7-12(20-11(3)18)8-17(4)6-5-13-10(2)16(19)21-15(13)14(9)17/h12-13,15H,2,5-8H2,1,3-4H3/t12-,13-,15+,17-/m0/s1
InChI Key DNUVCKQEOUHKDL-LBEHMCEESA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C17H22O4
Molecular Weight 290.40 g/mol
Exact Mass 290.15180918 g/mol
Topological Polar Surface Area (TPSA) 52.60 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.93
H-Bond Acceptor 4
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

Top
ACon0_000390
ACon1_000403
C17H22O4
NCGC00169110-01
BRD-K97233445-001-01-7

2D Structure

Top
2D Structure of [(3aS,5aS,7S,9bR)-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-7-yl] acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9940 99.40%
Caco-2 + 0.6552 65.52%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7147 71.47%
OATP2B1 inhibitior - 0.8554 85.54%
OATP1B1 inhibitior + 0.8480 84.80%
OATP1B3 inhibitior - 0.2429 24.29%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior - 0.8566 85.66%
P-glycoprotein inhibitior - 0.7957 79.57%
P-glycoprotein substrate - 0.8300 83.00%
CYP3A4 substrate + 0.6555 65.55%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.5163 51.63%
CYP2C9 inhibition - 0.8560 85.60%
CYP2C19 inhibition - 0.7927 79.27%
CYP2D6 inhibition - 0.9487 94.87%
CYP1A2 inhibition + 0.5050 50.50%
CYP2C8 inhibition - 0.6498 64.98%
CYP inhibitory promiscuity - 0.8434 84.34%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5935 59.35%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.6099 60.99%
Skin irritation + 0.5434 54.34%
Skin corrosion - 0.9128 91.28%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6398 63.98%
Micronuclear - 0.6200 62.00%
Hepatotoxicity + 0.6744 67.44%
skin sensitisation - 0.7565 75.65%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity + 0.7602 76.02%
Acute Oral Toxicity (c) III 0.7859 78.59%
Estrogen receptor binding - 0.5188 51.88%
Androgen receptor binding - 0.5739 57.39%
Thyroid receptor binding - 0.5469 54.69%
Glucocorticoid receptor binding + 0.6453 64.53%
Aromatase binding - 0.5807 58.07%
PPAR gamma - 0.6113 61.13%
Honey bee toxicity - 0.7057 70.57%
Biodegradation - 0.5250 52.50%
Crustacea aquatic toxicity - 0.5150 51.50%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.43% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.03% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.74% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 88.25% 97.79%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.74% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.28% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.04% 85.14%
CHEMBL2581 P07339 Cathepsin D 85.63% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.61% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.43% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 80.74% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.64% 89.00%

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.
Sphaeranthus suaveolens

Cross-Links

Top
PubChem 14589094
LOTUS LTS0112726
wikiData Q104985742