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

Details

• Internal ID: f1d476c9-4a0b-49e4-a026-0b0b11917057
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(4aR,8R,8aS,9aR)-3,5,8a-trimethyl-2,7-dioxo-4a,8,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-8-yl] acetate
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3C2)C)C)OC(=O)C
• SMILES (Isomeric): CC1=CC(=O)[C@@H]([C@@]2([C@@H]1CC3=C(C(=O)O[C@@H]3C2)C)C)OC(=O)C
• InChI: InChI=1S/C17H20O5/c1-8-5-13(19)15(21-10(3)18)17(4)7-14-11(6-12(8)17)9(2)16(20)22-14/h5,12,14-15H,6-7H2,1-4H3/t12-,14-,15+,17+/m1/s1
• InChI Key: OWLOPHNHXBLXJM-UTXMOHQDSA-N
• Popularity: 1 reference 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): 69.70 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 5
• 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	+	0.9955	99.55%
Caco-2	+	0.7474	74.74%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6831	68.31%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8657	86.57%
OATP1B3 inhibitior	+	0.9079	90.79%
MATE1 inhibitior	-	0.5800	58.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6199	61.99%
P-glycoprotein inhibitior	-	0.6652	66.52%
P-glycoprotein substrate	-	0.8491	84.91%
CYP3A4 substrate	+	0.6286	62.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9102	91.02%
CYP3A4 inhibition	+	0.5198	51.98%
CYP2C9 inhibition	-	0.8951	89.51%
CYP2C19 inhibition	-	0.8788	87.88%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.6914	69.14%
CYP2C8 inhibition	-	0.8180	81.80%
CYP inhibitory promiscuity	-	0.6977	69.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4384	43.84%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.7746	77.46%
Skin irritation	-	0.5432	54.32%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6688	66.88%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7131	71.31%
skin sensitisation	-	0.7261	72.61%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6573	65.73%
Acute Oral Toxicity (c)	III	0.6017	60.17%
Estrogen receptor binding	+	0.8070	80.70%
Androgen receptor binding	+	0.5588	55.88%
Thyroid receptor binding	-	0.6118	61.18%
Glucocorticoid receptor binding	-	0.5554	55.54%
Aromatase binding	-	0.7237	72.37%
PPAR gamma	+	0.5276	52.76%
Honey bee toxicity	-	0.7652	76.52%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9955	99.55%

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	97.16%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.89%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.37%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.20%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.38%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.82%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.68%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.29%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.12%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.82%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.22%	100.00%

Plants that contains it

• Salvia palaefolia

Cross-Links

• PubChem: 162999605
• LOTUS: LTS0120989
• wikiData: Q105202083