(3aS,5aR,6R,8R,9bS)-8-hydroperoxy-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 0322ab9d-ad44-49e1-97d6-ac3662c74bfb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aR,6R,8R,9bS)-8-hydroperoxy-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O5/c1-7-9-4-5-15(3)11(16)6-10(20-18)8(2)12(15)13(9)19-14(7)17/h9-11,13,16,18H,1,4-6H2,2-3H3/t9-,10+,11+,13-,15-/m0/s1
• InChI Key: LQSRPJKNQQPZHM-JRUNUNTISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.5907	59.07%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6711	67.11%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	+	0.8910	89.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7170	71.70%
BSEP inhibitior	-	0.9480	94.80%
P-glycoprotein inhibitior	-	0.8354	83.54%
P-glycoprotein substrate	-	0.8513	85.13%
CYP3A4 substrate	+	0.6444	64.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8393	83.93%
CYP3A4 inhibition	-	0.5595	55.95%
CYP2C9 inhibition	-	0.8205	82.05%
CYP2C19 inhibition	-	0.8031	80.31%
CYP2D6 inhibition	-	0.9250	92.50%
CYP1A2 inhibition	-	0.5778	57.78%
CYP2C8 inhibition	-	0.6150	61.50%
CYP inhibitory promiscuity	-	0.8154	81.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5049	50.49%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.7330	73.30%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8824	88.24%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5746	57.46%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8044	80.44%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6658	66.58%
Acute Oral Toxicity (c)	I	0.2987	29.87%
Estrogen receptor binding	+	0.6015	60.15%
Androgen receptor binding	+	0.5561	55.61%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5568	55.68%
Aromatase binding	-	0.6680	66.80%
PPAR gamma	-	0.5889	58.89%
Honey bee toxicity	-	0.6426	64.26%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9967	99.67%

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	93.31%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.89%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.74%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.64%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.56%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.26%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.22%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	87.99%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL259	P32245	Melanocortin receptor 4	83.20%	95.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.94%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.50%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.37%	94.00%

Plants that contains it

• Tanacetum praeteritum

Cross-Links

• PubChem: 71473708
• LOTUS: LTS0165443
• wikiData: Q105155768