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

Details

• Internal ID: 9284e9f2-7ca3-4755-9da4-35aa89565965
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (1S,3aR,5S,5aS,6S,8aS,9aR)-6-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,7-b]furan-2,8-dione
• InChI: InChI=1S/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7-11,13,16H,4-6H2,1-3H3/t7-,8-,9+,10-,11+,13+,15+/m0/s1
• InChI Key: IMDDBFKJQVMAMZ-QMCMGCPXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9660	96.60%
Caco-2	+	0.5498	54.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4800	48.00%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9130	91.30%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8792	87.92%
P-glycoprotein inhibitior	-	0.8802	88.02%
P-glycoprotein substrate	-	0.7187	71.87%
CYP3A4 substrate	+	0.5897	58.97%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8269	82.69%
CYP3A4 inhibition	-	0.8494	84.94%
CYP2C9 inhibition	-	0.8960	89.60%
CYP2C19 inhibition	-	0.9150	91.50%
CYP2D6 inhibition	-	0.9717	97.17%
CYP1A2 inhibition	-	0.7367	73.67%
CYP2C8 inhibition	-	0.8875	88.75%
CYP inhibitory promiscuity	-	0.9922	99.22%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6222	62.22%
Eye corrosion	-	0.9754	97.54%
Eye irritation	-	0.9148	91.48%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8219	82.19%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6124	61.24%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7712	77.12%
skin sensitisation	-	0.8363	83.63%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7538	75.38%
Acute Oral Toxicity (c)	II	0.4526	45.26%
Estrogen receptor binding	+	0.6396	63.96%
Androgen receptor binding	+	0.5304	53.04%
Thyroid receptor binding	-	0.5567	55.67%
Glucocorticoid receptor binding	-	0.7039	70.39%
Aromatase binding	-	0.8044	80.44%
PPAR gamma	-	0.7504	75.04%
Honey bee toxicity	-	0.7405	74.05%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9438	94.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.16%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.71%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.77%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	87.50%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.30%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.62%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	84.42%	98.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.04%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.61%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.25%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.59%	94.45%

Plants that contains it

• Stevia isomeca

Cross-Links

• PubChem: 162850391
• LOTUS: LTS0182210
• wikiData: Q105115598