(9-hydroxy-5a,9-dimethyl-3-methylidene-2,6-dioxo-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-4-yl) acetate

Details

• Internal ID: f4a1839b-cc5b-478e-a7ca-ccd54d5c5889
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (9-hydroxy-5a,9-dimethyl-3-methylidene-2,6-dioxo-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-4-yl) acetate
• InChI: InChI=1S/C17H20O6/c1-8-12-10(22-9(2)18)7-16(3)11(19)5-6-17(4,21)14(16)13(12)23-15(8)20/h5-6,10,12-14,21H,1,7H2,2-4H3
• InChI Key: CHLFYHWCCBYJGC-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 6
• 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	+	0.9790	97.90%
Caco-2	-	0.5321	53.21%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5927	59.27%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.8256	82.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9026	90.26%
P-glycoprotein inhibitior	-	0.7468	74.68%
P-glycoprotein substrate	-	0.7463	74.63%
CYP3A4 substrate	+	0.6274	62.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9120	91.20%
CYP3A4 inhibition	+	0.5235	52.35%
CYP2C9 inhibition	-	0.8324	83.24%
CYP2C19 inhibition	-	0.8612	86.12%
CYP2D6 inhibition	-	0.9658	96.58%
CYP1A2 inhibition	-	0.6993	69.93%
CYP2C8 inhibition	-	0.8024	80.24%
CYP inhibitory promiscuity	-	0.6931	69.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.3776	37.76%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.8753	87.53%
Skin irritation	-	0.5617	56.17%
Skin corrosion	-	0.9064	90.64%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5961	59.61%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6591	65.91%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5719	57.19%
Acute Oral Toxicity (c)	III	0.3392	33.92%
Estrogen receptor binding	+	0.7007	70.07%
Androgen receptor binding	+	0.5812	58.12%
Thyroid receptor binding	+	0.6381	63.81%
Glucocorticoid receptor binding	+	0.5484	54.84%
Aromatase binding	-	0.6152	61.52%
PPAR gamma	+	0.5584	55.84%
Honey bee toxicity	-	0.7581	75.81%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9874	98.74%

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	97.40%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.22%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.19%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.02%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.57%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.34%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.26%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.56%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.76%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.99%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.82%	91.07%
CHEMBL221	P23219	Cyclooxygenase-1	81.16%	90.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.46%	92.94%

Plants that contains it

• Artemisia ludoviciana subsp. mexicana

Cross-Links

• PubChem: 162863219
• LOTUS: LTS0015887
• wikiData: Q104396944