[(4aR,8R,8aS,9aR)-9a-hydroxy-3,5,8a-trimethyl-2,7-dioxo-4,4a,8,9-tetrahydrobenzo[f][1]benzofuran-8-yl] acetate

Details

• Internal ID: b2cf613a-c370-48cb-bd9f-42cf173f4a6b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(4aR,8R,8aS,9aR)-9a-hydroxy-3,5,8a-trimethyl-2,7-dioxo-4,4a,8,9-tetrahydrobenzo[f][1]benzofuran-8-yl] acetate
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3(C2)O)C)C)OC(=O)C
• SMILES (Isomeric): CC1=CC(=O)[C@@H]([C@@]2([C@@H]1CC3=C(C(=O)O[C@@]3(C2)O)C)C)OC(=O)C
• InChI: InChI=1S/C17H20O6/c1-8-5-13(19)14(22-10(3)18)16(4)7-17(21)12(6-11(8)16)9(2)15(20)23-17/h5,11,14,21H,6-7H2,1-4H3/t11-,14+,16+,17-/m1/s1
• InChI Key: LIFBCCDKWRTEGI-RNCIANSQSA-N
• Popularity: 1 reference 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: 0.50
• Atomic LogP (AlogP): 1.43
• 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	+	0.9955	99.55%
Caco-2	+	0.6249	62.49%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6923	69.23%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8760	87.60%
OATP1B3 inhibitior	+	0.8929	89.29%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7439	74.39%
P-glycoprotein inhibitior	-	0.7921	79.21%
P-glycoprotein substrate	-	0.7924	79.24%
CYP3A4 substrate	+	0.6418	64.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8946	89.46%
CYP3A4 inhibition	-	0.5201	52.01%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.9139	91.39%
CYP2D6 inhibition	-	0.9622	96.22%
CYP1A2 inhibition	-	0.7819	78.19%
CYP2C8 inhibition	-	0.7369	73.69%
CYP inhibitory promiscuity	-	0.9145	91.45%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4211	42.11%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8058	80.58%
Skin irritation	+	0.5390	53.90%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6728	67.28%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.6154	61.54%
skin sensitisation	-	0.7964	79.64%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7451	74.51%
Acute Oral Toxicity (c)	III	0.3332	33.32%
Estrogen receptor binding	+	0.8000	80.00%
Androgen receptor binding	+	0.6043	60.43%
Thyroid receptor binding	+	0.5543	55.43%
Glucocorticoid receptor binding	+	0.5712	57.12%
Aromatase binding	-	0.6402	64.02%
PPAR gamma	+	0.6494	64.94%
Honey bee toxicity	-	0.7670	76.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9898	98.98%

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	98.07%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.68%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.18%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.67%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.40%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.02%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.56%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL5028	O14672	ADAM10	81.76%	97.50%

Plants that contains it

• Salvia palaefolia

Cross-Links

• PubChem: 14733748
• LOTUS: LTS0157204
• wikiData: Q105152157