[(3aS,5R,5aS,8aR,9S,9aS)-5-methyl-1-methylidene-2,8-dioxo-4,5,5a,6,7,8a,9,9a-octahydro-3aH-azuleno[6,5-b]furan-9-yl] acetate

Details

• Internal ID: 7bce7ecc-911c-414e-a1c4-f94e088606e4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aS,5R,5aS,8aR,9S,9aS)-5-methyl-1-methylidene-2,8-dioxo-4,5,5a,6,7,8a,9,9a-octahydro-3aH-azuleno[6,5-b]furan-9-yl] acetate
• InChI: InChI=1S/C16H20O5/c1-7-6-12-13(8(2)16(19)21-12)15(20-9(3)17)14-10(7)4-5-11(14)18/h7,10,12-15H,2,4-6H2,1,3H3/t7-,10+,12+,13+,14+,15+/m1/s1
• InChI Key: YQURDSNGRPRTJQ-MPMBALMWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.33 g/mol
• Exact Mass: 292.13107373 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	+	0.7740	77.40%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5796	57.96%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.8617	86.17%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9061	90.61%
P-glycoprotein inhibitior	-	0.7624	76.24%
P-glycoprotein substrate	-	0.8551	85.51%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.7298	72.98%
CYP2C9 inhibition	-	0.8603	86.03%
CYP2C19 inhibition	-	0.7642	76.42%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	+	0.7323	73.23%
CYP2C8 inhibition	-	0.7903	79.03%
CYP inhibitory promiscuity	-	0.8932	89.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6701	67.01%
Eye corrosion	-	0.9451	94.51%
Eye irritation	+	0.5231	52.31%
Skin irritation	-	0.5562	55.62%
Skin corrosion	-	0.9123	91.23%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6857	68.57%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.7676	76.76%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4495	44.95%
Acute Oral Toxicity (c)	III	0.4025	40.25%
Estrogen receptor binding	+	0.5982	59.82%
Androgen receptor binding	+	0.5701	57.01%
Thyroid receptor binding	-	0.5879	58.79%
Glucocorticoid receptor binding	-	0.5100	51.00%
Aromatase binding	-	0.6493	64.93%
PPAR gamma	-	0.6047	60.47%
Honey bee toxicity	-	0.7495	74.95%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9956	99.56%

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	94.45%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.63%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.47%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.16%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.47%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.86%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.86%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.88%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.72%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.55%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.58%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	80.53%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.52%	91.19%

Plants that contains it

• Rhanteriopsis bombycina

Cross-Links

• PubChem: 162881351
• LOTUS: LTS0211668
• wikiData: Q105352585