(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

• 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

• 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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

• Aucklandia costus

Cross-Links

• PubChem: 15386529
• LOTUS: LTS0175254
• wikiData: Q104982160