[(3aR,4S,6aS,9aR,9bS)-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate

Details

• Internal ID: 3da3a9b0-5d25-4027-bd54-d454f5757f24
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aS,9aR,9bS)-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
• InChI: InChI=1S/C17H20O5/c1-8-5-6-17(20)9(2)7-12(21-11(4)18)13-10(3)16(19)22-15(13)14(8)17/h5,12-15,20H,2-3,6-7H2,1,4H3/t12-,13+,14+,15-,17+/m0/s1
• InChI Key: YFKYWMBSLLLPGV-SOXILONMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.34 g/mol
• Exact Mass: 304.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	-	0.5620	56.20%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6134	61.34%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9242	92.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9551	95.51%
P-glycoprotein inhibitior	-	0.7568	75.68%
P-glycoprotein substrate	-	0.7782	77.82%
CYP3A4 substrate	+	0.6243	62.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8958	89.58%
CYP3A4 inhibition	-	0.6076	60.76%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.9566	95.66%
CYP1A2 inhibition	-	0.7492	74.92%
CYP2C8 inhibition	-	0.7494	74.94%
CYP inhibitory promiscuity	-	0.9577	95.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Non-required	0.5566	55.66%
Eye corrosion	-	0.9673	96.73%
Eye irritation	-	0.8111	81.11%
Skin irritation	-	0.5717	57.17%
Skin corrosion	-	0.8562	85.62%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4919	49.19%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7370	73.70%
skin sensitisation	-	0.6948	69.48%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6762	67.62%
Acute Oral Toxicity (c)	II	0.4460	44.60%
Estrogen receptor binding	+	0.6297	62.97%
Androgen receptor binding	+	0.6145	61.45%
Thyroid receptor binding	+	0.5959	59.59%
Glucocorticoid receptor binding	+	0.5675	56.75%
Aromatase binding	-	0.6908	69.08%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7479	74.79%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5750	57.50%
Fish aquatic toxicity	+	0.9755	97.55%

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	96.04%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.97%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.79%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.48%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.77%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.68%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.66%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.36%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.22%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.14%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.69%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.66%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.56%	95.89%

Plants that contains it

• Artemisia gmelinii

Cross-Links

• PubChem: 49799784
• LOTUS: LTS0222107
• wikiData: Q105347645