[(E)-[(3aR,4S,5aR,9aS,9bR)-4-acetyloxy-5a-methyl-3-methylidene-2,6-dioxo-4,5,7,8,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-9-ylidene]methyl] acetate

Details

• Internal ID: 2fab425f-585a-4431-a8dd-af71e96f59dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(E)-[(3aR,4S,5aR,9aS,9bR)-4-acetyloxy-5a-methyl-3-methylidene-2,6-dioxo-4,5,7,8,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-9-ylidene]methyl] acetate
• InChI: InChI=1S/C19H22O7/c1-9-15-13(25-11(3)21)7-19(4)14(22)6-5-12(8-24-10(2)20)16(19)17(15)26-18(9)23/h8,13,15-17H,1,5-7H2,2-4H3/b12-8+/t13-,15+,16+,17-,19-/m0/s1
• InChI Key: GAWZFNSNYXHYKY-NDKKMENKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₇
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.13655304 g/mol
• Topological Polar Surface Area (TPSA): 96.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.5382	53.82%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6433	64.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	-	0.3172	31.72%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5427	54.27%
P-glycoprotein substrate	-	0.8197	81.97%
CYP3A4 substrate	+	0.6430	64.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8877	88.77%
CYP3A4 inhibition	-	0.5469	54.69%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.7835	78.35%
CYP2D6 inhibition	-	0.9648	96.48%
CYP1A2 inhibition	+	0.5638	56.38%
CYP2C8 inhibition	-	0.6402	64.02%
CYP inhibitory promiscuity	-	0.8531	85.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5825	58.25%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.7711	77.11%
Skin irritation	+	0.5547	55.47%
Skin corrosion	-	0.8864	88.64%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6006	60.06%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.7612	76.12%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6630	66.30%
Acute Oral Toxicity (c)	III	0.5351	53.51%
Estrogen receptor binding	+	0.6715	67.15%
Androgen receptor binding	+	0.6374	63.74%
Thyroid receptor binding	-	0.5100	51.00%
Glucocorticoid receptor binding	+	0.7403	74.03%
Aromatase binding	-	0.7333	73.33%
PPAR gamma	+	0.5958	59.58%
Honey bee toxicity	-	0.6864	68.64%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.13%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.78%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.74%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.05%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	87.87%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.77%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.37%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.66%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.36%	96.09%

Plants that contains it

• Cyanthillium cinereum

Cross-Links

• PubChem: 162953166
• LOTUS: LTS0055807
• wikiData: Q105005687