9-hydroperoxy-5a,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-2,6-dione

Details

• Internal ID: 3921aba4-9b76-4bbb-b1c6-043acf4fd393
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 9-hydroperoxy-5a,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-benzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC12CCC3C(C1C(C=CC2=O)(C)OO)OC(=O)C3=C
• SMILES (Isomeric): CC12CCC3C(C1C(C=CC2=O)(C)OO)OC(=O)C3=C
• InChI: InChI=1S/C15H18O5/c1-8-9-4-6-14(2)10(16)5-7-15(3,20-18)12(14)11(9)19-13(8)17/h5,7,9,11-12,18H,1,4,6H2,2-3H3
• InChI Key: UYWMGHBFAYXXMR-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): 72.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	+	0.6126	61.26%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5338	53.38%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8338	83.38%
OATP1B3 inhibitior	+	0.8599	85.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	-	0.8989	89.89%
P-glycoprotein inhibitior	-	0.8797	87.97%
P-glycoprotein substrate	-	0.8601	86.01%
CYP3A4 substrate	+	0.6190	61.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8932	89.32%
CYP3A4 inhibition	-	0.6681	66.81%
CYP2C9 inhibition	-	0.7943	79.43%
CYP2C19 inhibition	-	0.8592	85.92%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	+	0.5638	56.38%
CYP2C8 inhibition	-	0.5842	58.42%
CYP inhibitory promiscuity	-	0.7558	75.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4885	48.85%
Eye corrosion	-	0.9717	97.17%
Eye irritation	-	0.8740	87.40%
Skin irritation	-	0.5581	55.81%
Skin corrosion	-	0.8029	80.29%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5802	58.02%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6713	67.13%
skin sensitisation	-	0.7123	71.23%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5470	54.70%
Acute Oral Toxicity (c)	III	0.4879	48.79%
Estrogen receptor binding	+	0.6163	61.63%
Androgen receptor binding	+	0.6408	64.08%
Thyroid receptor binding	+	0.6220	62.20%
Glucocorticoid receptor binding	-	0.5150	51.50%
Aromatase binding	-	0.7424	74.24%
PPAR gamma	-	0.6169	61.69%
Honey bee toxicity	-	0.8593	85.93%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	96.37%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.01%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.19%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.08%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.94%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.79%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.05%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.37%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.03%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	82.12%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.34%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.45%	98.95%

Plants that contains it

• Achillea millefolium

Cross-Links

• PubChem: 162995470
• LOTUS: LTS0260567
• wikiData: Q105281997