5,8-Dihydroxy-5,8a-dimethyl-3-methylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: d957f92f-dcbc-44dd-8e6b-041a8da20c71
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 5,8-dihydroxy-5,8a-dimethyl-3-methylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1(CCC(C2(C1=CC3C(C2)OC(=O)C3=C)C)O)O
• SMILES (Isomeric): CC1(CCC(C2(C1=CC3C(C2)OC(=O)C3=C)C)O)O
• InChI: InChI=1S/C15H20O4/c1-8-9-6-11-14(2,7-10(9)19-13(8)17)12(16)4-5-15(11,3)18/h6,9-10,12,16,18H,1,4-5,7H2,2-3H3
• InChI Key: DGKQNKHPXPFURS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	+	0.7027	70.27%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9055	90.55%
OATP1B3 inhibitior	+	0.8900	89.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5420	54.20%
BSEP inhibitior	-	0.9762	97.62%
P-glycoprotein inhibitior	-	0.9142	91.42%
P-glycoprotein substrate	-	0.8402	84.02%
CYP3A4 substrate	+	0.6068	60.68%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.5466	54.66%
CYP2C9 inhibition	-	0.9303	93.03%
CYP2C19 inhibition	-	0.8991	89.91%
CYP2D6 inhibition	-	0.9311	93.11%
CYP1A2 inhibition	-	0.6811	68.11%
CYP2C8 inhibition	-	0.7884	78.84%
CYP inhibitory promiscuity	-	0.8977	89.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5100	51.00%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8643	86.43%
Skin irritation	+	0.6167	61.67%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6579	65.79%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.7732	77.32%
skin sensitisation	-	0.7553	75.53%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6093	60.93%
Acute Oral Toxicity (c)	III	0.4868	48.68%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5208	52.08%
Thyroid receptor binding	+	0.5805	58.05%
Glucocorticoid receptor binding	-	0.4775	47.75%
Aromatase binding	-	0.5116	51.16%
PPAR gamma	-	0.6577	65.77%
Honey bee toxicity	-	0.8548	85.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	91.80%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.05%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.51%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.37%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.43%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.48%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.33%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	84.63%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.36%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.49%	95.89%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 75581810
• LOTUS: LTS0013630
• wikiData: Q104978827