(3R,3aR,6aR,9aR,9bR)-6,9-dimethylidenespiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,2'-oxirane]-2,8-dione

Details

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Internal ID 0f39c019-f39b-4f8f-9c91-d98b5a358920
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3R,3aR,6aR,9aR,9bR)-6,9-dimethylidenespiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,2'-oxirane]-2,8-dione
SMILES (Canonical) C=C1CCC2C(C3C1CC(=O)C3=C)OC(=O)C24CO4
SMILES (Isomeric) C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CC(=O)C3=C)OC(=O)[C@]24CO4
InChI InChI=1S/C15H16O4/c1-7-3-4-10-13(19-14(17)15(10)6-18-15)12-8(2)11(16)5-9(7)12/h9-10,12-13H,1-6H2/t9-,10+,12-,13-,15-/m0/s1
InChI Key DJGLGXXXPMRUCU-BOWTYGHESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H16O4
Molecular Weight 260.28 g/mol
Exact Mass 260.10485899 g/mol
Topological Polar Surface Area (TPSA) 55.90 Ų
XlogP 0.80
Atomic LogP (AlogP) 1.41
H-Bond Acceptor 4
H-Bond Donor 0
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,3aR,6aR,9aR,9bR)-6,9-dimethylidenespiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,2'-oxirane]-2,8-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9801 98.01%
Caco-2 - 0.5331 53.31%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.7425 74.25%
OATP2B1 inhibitior - 0.8571 85.71%
OATP1B1 inhibitior + 0.8993 89.93%
OATP1B3 inhibitior + 0.9659 96.59%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior - 0.8936 89.36%
P-glycoprotein inhibitior - 0.8946 89.46%
P-glycoprotein substrate - 0.7715 77.15%
CYP3A4 substrate + 0.5393 53.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8518 85.18%
CYP3A4 inhibition - 0.9045 90.45%
CYP2C9 inhibition - 0.8768 87.68%
CYP2C19 inhibition - 0.8797 87.97%
CYP2D6 inhibition - 0.9193 91.93%
CYP1A2 inhibition - 0.6795 67.95%
CYP2C8 inhibition - 0.7774 77.74%
CYP inhibitory promiscuity - 0.9554 95.54%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9243 92.43%
Carcinogenicity (trinary) Non-required 0.6113 61.13%
Eye corrosion - 0.9337 93.37%
Eye irritation + 0.6249 62.49%
Skin irritation - 0.6890 68.90%
Skin corrosion - 0.9017 90.17%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7751 77.51%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.8625 86.25%
skin sensitisation - 0.7379 73.79%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity + 0.9171 91.71%
Acute Oral Toxicity (c) III 0.4653 46.53%
Estrogen receptor binding + 0.6399 63.99%
Androgen receptor binding + 0.6226 62.26%
Thyroid receptor binding - 0.5710 57.10%
Glucocorticoid receptor binding + 0.6043 60.43%
Aromatase binding - 0.7284 72.84%
PPAR gamma - 0.6508 65.08%
Honey bee toxicity - 0.5791 57.91%
Biodegradation - 0.6000 60.00%
Crustacea aquatic toxicity + 0.6700 67.00%
Fish aquatic toxicity + 0.9447 94.47%

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 93.73% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.87% 97.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.67% 92.94%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.84% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.08% 95.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.87% 93.04%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.82% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.12% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.42% 95.89%
CHEMBL1902 P62942 FK506-binding protein 1A 80.08% 97.05%

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.
Aucklandia costus

Cross-Links

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PubChem 15386529
LOTUS LTS0175254
wikiData Q104982160