PlantaeDB Logo
Login Sign-up

[(3aR,4S,5aR,6S,9S,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (Z)-4-acetyloxy-2-methylbut-2-enoate

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

Top
Internal ID 26774314-cb05-45f5-9413-3deb46223576
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aR,6S,9S,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (Z)-4-acetyloxy-2-methylbut-2-enoate
SMILES (Canonical) CC(=CCOC(=O)C)C(=O)OC1CCC2(CO2)C3C1(CC(C4C3OC(=O)C4=C)O)C
SMILES (Isomeric) C/C(=C/COC(=O)C)/C(=O)O[C@H]1CC[C@@]2(CO2)[C@H]3[C@]1(C[C@@H]([C@@H]4[C@@H]3OC(=O)C4=C)O)C
InChI InChI=1S/C22H28O8/c1-11(6-8-27-13(3)23)19(25)29-15-5-7-22(10-28-22)18-17-16(12(2)20(26)30-17)14(24)9-21(15,18)4/h6,14-18,24H,2,5,7-10H2,1,3-4H3/b11-6-/t14-,15-,16+,17-,18+,21-,22+/m0/s1
InChI Key XEBIHJVLTHUZQM-CLAHRCANSA-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) 112.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 1.46
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(3aR,4S,5aR,6S,9S,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (Z)-4-acetyloxy-2-methylbut-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9793 97.93%
Caco-2 - 0.6364 63.64%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.7452 74.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8651 86.51%
OATP1B3 inhibitior + 0.9368 93.68%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5021 50.21%
BSEP inhibitior + 0.7806 78.06%
P-glycoprotein inhibitior - 0.4756 47.56%
P-glycoprotein substrate - 0.6210 62.10%
CYP3A4 substrate + 0.6902 69.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8932 89.32%
CYP3A4 inhibition - 0.5604 56.04%
CYP2C9 inhibition - 0.7823 78.23%
CYP2C19 inhibition - 0.8582 85.82%
CYP2D6 inhibition - 0.9375 93.75%
CYP1A2 inhibition - 0.8118 81.18%
CYP2C8 inhibition - 0.6022 60.22%
CYP inhibitory promiscuity - 0.9349 93.49%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5105 51.05%
Eye corrosion - 0.9869 98.69%
Eye irritation - 0.9450 94.50%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9221 92.21%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4290 42.90%
Micronuclear - 0.6500 65.00%
Hepatotoxicity + 0.6413 64.13%
skin sensitisation - 0.8220 82.20%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.8873 88.73%
Acute Oral Toxicity (c) I 0.4680 46.80%
Estrogen receptor binding + 0.7729 77.29%
Androgen receptor binding + 0.6579 65.79%
Thyroid receptor binding - 0.5657 56.57%
Glucocorticoid receptor binding + 0.7861 78.61%
Aromatase binding + 0.6565 65.65%
PPAR gamma + 0.7003 70.03%
Honey bee toxicity - 0.7162 71.62%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9933 99.33%

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 98.61% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.88% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.93% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.98% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 91.76% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.48% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.12% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.03% 99.23%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.13% 97.28%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.93% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.43% 92.62%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.35% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.34% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.45% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.33% 92.94%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.22% 91.07%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.02% 100.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 81.39% 98.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.00% 85.14%
CHEMBL5957 P21589 5'-nucleotidase 80.92% 97.78%

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.
Dimerostemma brasilianum

Cross-Links

Top
PubChem 162906076
LOTUS LTS0157363
wikiData Q105326220