8,9a-Dihydroxy-3,5,8a-trimethyl-4,4a,8,9-tetrahydrobenzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: 688d23d3-035b-4481-b0c4-445fa9f6db09
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 8,9a-dihydroxy-3,5,8a-trimethyl-4,4a,8,9-tetrahydrobenzo[f][1]benzofuran-2,7-dione
• SMILES (Canonical): CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3(C2)O)C)C)O
• SMILES (Isomeric): CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3(C2)O)C)C)O
• InChI: InChI=1S/C15H18O5/c1-7-4-11(16)12(17)14(3)6-15(19)10(5-9(7)14)8(2)13(18)20-15/h4,9,12,17,19H,5-6H2,1-3H3
• InChI Key: JLKSXTRHPGICRR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.85
• H-Bond Acceptor: 5
• 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	+	0.9912	99.12%
Caco-2	-	0.5728	57.28%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6947	69.47%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8589	85.89%
P-glycoprotein inhibitior	-	0.9444	94.44%
P-glycoprotein substrate	-	0.7993	79.93%
CYP3A4 substrate	+	0.6002	60.02%
CYP2C9 substrate	-	0.7908	79.08%
CYP2D6 substrate	-	0.8845	88.45%
CYP3A4 inhibition	-	0.5831	58.31%
CYP2C9 inhibition	-	0.8932	89.32%
CYP2C19 inhibition	-	0.9117	91.17%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.7985	79.85%
CYP2C8 inhibition	-	0.9007	90.07%
CYP inhibitory promiscuity	-	0.9108	91.08%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4388	43.88%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8039	80.39%
Skin irritation	+	0.6319	63.19%
Skin corrosion	-	0.8937	89.37%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5615	56.15%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.8068	80.68%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5974	59.74%
Acute Oral Toxicity (c)	I	0.4724	47.24%
Estrogen receptor binding	+	0.5375	53.75%
Androgen receptor binding	+	0.5738	57.38%
Thyroid receptor binding	+	0.5515	55.15%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6938	69.38%
PPAR gamma	+	0.5364	53.64%
Honey bee toxicity	-	0.8889	88.89%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9897	98.97%

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	97.49%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.09%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.34%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.27%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.63%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.86%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	84.81%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.21%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.11%	97.09%
CHEMBL4208	P20618	Proteasome component C5	80.81%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	80.45%	94.73%

Plants that contains it

• Salvia palaefolia

Cross-Links

• PubChem: 14733751
• LOTUS: LTS0264257
• wikiData: Q105130847