[(3aS,6aR,8S,9R,9aR,9bR)-8-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[8,7-b]furan-9-yl]methyl acetate

Details

• Internal ID: 5198c86f-5c2a-4893-a91e-22d3b26c416a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aS,6aR,8S,9R,9aR,9bR)-8-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[8,7-b]furan-9-yl]methyl acetate
• InChI: InChI=1S/C17H22O5/c1-8-4-5-11-9(2)17(20)22-16(11)15-12(8)6-14(19)13(15)7-21-10(3)18/h11-16,19H,1-2,4-7H2,3H3/t11-,12-,13+,14-,15+,16-/m0/s1
• InChI Key: JZLNEGYYSYMRBG-KLOLGFOXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	-	0.5992	59.92%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7523	75.23%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8400	84.00%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6570	65.70%
BSEP inhibitior	-	0.7250	72.50%
P-glycoprotein inhibitior	-	0.8226	82.26%
P-glycoprotein substrate	-	0.8200	82.00%
CYP3A4 substrate	+	0.6041	60.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.8599	85.99%
CYP2C9 inhibition	-	0.8560	85.60%
CYP2C19 inhibition	-	0.8279	82.79%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.6187	61.87%
CYP2C8 inhibition	-	0.7284	72.84%
CYP inhibitory promiscuity	-	0.9333	93.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7250	72.50%
Eye corrosion	-	0.9569	95.69%
Eye irritation	-	0.6577	65.77%
Skin irritation	-	0.6406	64.06%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7006	70.06%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.7302	73.02%
skin sensitisation	-	0.8173	81.73%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5273	52.73%
Acute Oral Toxicity (c)	III	0.4746	47.46%
Estrogen receptor binding	+	0.6175	61.75%
Androgen receptor binding	+	0.6090	60.90%
Thyroid receptor binding	-	0.5629	56.29%
Glucocorticoid receptor binding	+	0.6711	67.11%
Aromatase binding	-	0.6007	60.07%
PPAR gamma	-	0.7150	71.50%
Honey bee toxicity	-	0.8129	81.29%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9742	97.42%

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	97.55%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.92%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.64%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.35%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	88.46%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.40%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	85.69%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	85.14%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.93%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.79%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.34%	99.17%

Plants that contains it

• Echinops spinosissimus subsp. neumayeri

Cross-Links

• PubChem: 21579288
• LOTUS: LTS0224833
• wikiData: Q105137464