(1S,3aR,5S,5aR,8aS,9aR)-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione

Details

• Internal ID: aca256e3-0410-4355-bc6b-0bfe8a3dd5f7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (1S,3aR,5S,5aR,8aS,9aR)-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione
• InChI: InChI=1S/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h4-5,8-12H,6-7H2,1-3H3/t8-,9-,10+,11-,12+,15-/m0/s1
• InChI Key: BRWKHHBGGUZQJZ-PEZSEORZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 3
• 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	+	0.9941	99.41%
Caco-2	+	0.6739	67.39%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5492	54.92%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7912	79.12%
P-glycoprotein inhibitior	-	0.8938	89.38%
P-glycoprotein substrate	-	0.7549	75.49%
CYP3A4 substrate	+	0.5696	56.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.8995	89.95%
CYP2C9 inhibition	-	0.9276	92.76%
CYP2C19 inhibition	-	0.8681	86.81%
CYP2D6 inhibition	-	0.9712	97.12%
CYP1A2 inhibition	-	0.7160	71.60%
CYP2C8 inhibition	-	0.8730	87.30%
CYP inhibitory promiscuity	-	0.9680	96.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9117	91.17%
Carcinogenicity (trinary)	Non-required	0.5894	58.94%
Eye corrosion	-	0.9523	95.23%
Eye irritation	-	0.9113	91.13%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8402	84.02%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6103	61.03%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.5590	55.90%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5238	52.38%
Acute Oral Toxicity (c)	III	0.5243	52.43%
Estrogen receptor binding	-	0.6846	68.46%
Androgen receptor binding	-	0.5974	59.74%
Thyroid receptor binding	-	0.6803	68.03%
Glucocorticoid receptor binding	-	0.7397	73.97%
Aromatase binding	-	0.7863	78.63%
PPAR gamma	-	0.8252	82.52%
Honey bee toxicity	-	0.7383	73.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9866	98.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.07%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.93%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.01%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.84%	85.14%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	88.82%	95.72%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.75%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.70%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.43%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.09%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.19%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.22%	85.30%

Plants that contains it

• Stevia isomeca

Cross-Links

• PubChem: 163044662
• LOTUS: LTS0039313
• wikiData: Q104945054