(4aS,5R,8aR,9aR)-9a-ethoxy-3,4a,5-trimethyl-4,5,8a,9-tetrahydrobenzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 6dc134c0-e888-427c-8ebb-b0c2aa6dfa9d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aS,5R,8aR,9aR)-9a-ethoxy-3,4a,5-trimethyl-4,5,8a,9-tetrahydrobenzo[f][1]benzofuran-2,6-dione
• SMILES (Canonical): CCOC12CC3C=CC(=O)C(C3(CC1=C(C(=O)O2)C)C)C
• SMILES (Isomeric): CCO[C@@]12C[C@@H]3C=CC(=O)[C@@H]([C@]3(CC1=C(C(=O)O2)C)C)C
• InChI: InChI=1S/C17H22O4/c1-5-20-17-8-12-6-7-14(18)11(3)16(12,4)9-13(17)10(2)15(19)21-17/h6-7,11-12H,5,8-9H2,1-4H3/t11-,12-,16+,17+/m0/s1
• InChI Key: KWLFGLJLUXQRAT-IYVPYFHTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.15180918 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 4
• 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	+	1.0000	100.00%
Caco-2	+	0.7610	76.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7104	71.04%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8388	83.88%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5955	59.55%
P-glycoprotein inhibitior	-	0.8356	83.56%
P-glycoprotein substrate	-	0.6844	68.44%
CYP3A4 substrate	+	0.6548	65.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8980	89.80%
CYP3A4 inhibition	-	0.6616	66.16%
CYP2C9 inhibition	-	0.7730	77.30%
CYP2C19 inhibition	-	0.7417	74.17%
CYP2D6 inhibition	-	0.9588	95.88%
CYP1A2 inhibition	-	0.7538	75.38%
CYP2C8 inhibition	-	0.7735	77.35%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5292	52.92%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9237	92.37%
Skin irritation	-	0.5162	51.62%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7164	71.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.3841	38.41%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5051	50.51%
skin sensitisation	-	0.8262	82.62%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6687	66.87%
Acute Oral Toxicity (c)	III	0.6896	68.96%
Estrogen receptor binding	-	0.5466	54.66%
Androgen receptor binding	+	0.5715	57.15%
Thyroid receptor binding	+	0.5431	54.31%
Glucocorticoid receptor binding	-	0.6339	63.39%
Aromatase binding	-	0.8099	80.99%
PPAR gamma	+	0.5541	55.41%
Honey bee toxicity	-	0.8246	82.46%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
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
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.06%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.09%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.37%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.30%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.49%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.03%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.09%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.01%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.63%	97.14%

Plants that contains it

• Senecio nemorensis

Cross-Links

• PubChem: 162897203
• LOTUS: LTS0150223
• wikiData: Q105147002