(4aS,8aR,9aS)-9a-hydroxy-3,5,8a-trimethyl-4a,9-dihydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 46cdc7dc-184b-440c-a5e5-0c289817ca28
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8aR,9aS)-9a-hydroxy-3,5,8a-trimethyl-4a,9-dihydro-4H-benzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4-6,11,17H,7-8H2,1-3H3/t11-,14-,15-/m0/s1
• InChI Key: LIYWCRLSRYPRBF-CQDKDKBSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

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	+	0.7693	76.93%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6139	61.39%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8953	89.53%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6118	61.18%
P-glycoprotein inhibitior	-	0.9481	94.81%
P-glycoprotein substrate	-	0.8524	85.24%
CYP3A4 substrate	+	0.5783	57.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.6990	69.90%
CYP2C9 inhibition	-	0.9027	90.27%
CYP2C19 inhibition	-	0.8911	89.11%
CYP2D6 inhibition	-	0.9673	96.73%
CYP1A2 inhibition	-	0.7211	72.11%
CYP2C8 inhibition	-	0.8305	83.05%
CYP inhibitory promiscuity	-	0.8817	88.17%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.3872	38.72%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8503	85.03%
Skin irritation	+	0.5690	56.90%
Skin corrosion	-	0.9082	90.82%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4919	49.19%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.7985	79.85%
skin sensitisation	-	0.6546	65.46%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6799	67.99%
Acute Oral Toxicity (c)	III	0.3650	36.50%
Estrogen receptor binding	-	0.6792	67.92%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5132	51.32%
Glucocorticoid receptor binding	-	0.6892	68.92%
Aromatase binding	-	0.7104	71.04%
PPAR gamma	+	0.6371	63.71%
Honey bee toxicity	-	0.8655	86.55%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9845	98.45%

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	95.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.32%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.24%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.61%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.51%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.82%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.57%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	82.63%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.60%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.56%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	80.25%	83.82%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10966804
• LOTUS: LTS0058823
• wikiData: Q105152434