[(3aS,5aR,7S,8aR,9aR)-1,5,8-trimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-7-yl] acetate

Details

• Internal ID: 5d4c96f7-df82-4292-b013-5b9c4d34d935
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aS,5aR,7S,8aR,9aR)-1,5,8-trimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-7-yl] acetate
• InChI: InChI=1S/C17H20O4/c1-8-5-16-14(10(3)17(19)21-16)6-13-9(2)15(7-12(8)13)20-11(4)18/h12-16H,1-3,5-7H2,4H3/t12-,13-,14+,15-,16-/m0/s1
• InChI Key: VHEGBMSVVODJTJ-QMHWVQJVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288.34 g/mol
• Exact Mass: 288.13615911 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 4
• 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	+	0.9907	99.07%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6419	64.19%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8872	88.72%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8934	89.34%
P-glycoprotein inhibitior	-	0.8046	80.46%
P-glycoprotein substrate	-	0.7854	78.54%
CYP3A4 substrate	+	0.5772	57.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.7940	79.40%
CYP2C9 inhibition	-	0.8486	84.86%
CYP2C19 inhibition	-	0.6831	68.31%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.5915	59.15%
CYP2C8 inhibition	-	0.7802	78.02%
CYP inhibitory promiscuity	-	0.8003	80.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9185	91.85%
Carcinogenicity (trinary)	Non-required	0.5879	58.79%
Eye corrosion	-	0.8875	88.75%
Eye irritation	-	0.5448	54.48%
Skin irritation	-	0.6695	66.95%
Skin corrosion	-	0.9192	91.92%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6286	62.86%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.6023	60.23%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7303	73.03%
Acute Oral Toxicity (c)	III	0.5361	53.61%
Estrogen receptor binding	+	0.6027	60.27%
Androgen receptor binding	+	0.5208	52.08%
Thyroid receptor binding	-	0.5775	57.75%
Glucocorticoid receptor binding	+	0.8109	81.09%
Aromatase binding	-	0.5405	54.05%
PPAR gamma	-	0.5854	58.54%
Honey bee toxicity	-	0.6270	62.70%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9880	98.80%

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	92.21%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.23%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	87.34%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.21%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.94%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.73%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	83.11%	95.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL2581	P07339	Cathepsin D	82.63%	98.95%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.11%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.44%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.42%	91.19%

Plants that contains it

• Arctotis auriculata

Cross-Links

• PubChem: 14466174
• LOTUS: LTS0043004
• wikiData: Q105286345