(6a-hydroperoxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) acetate

Details

• Internal ID: 71ddec2c-8140-465e-ac0a-c5377238430f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6a-hydroperoxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) acetate
• SMILES (Canonical): CC1=CCC2(C1C3C(C(C=C2C)OC(=O)C)C(=C)C(=O)O3)OO
• SMILES (Isomeric): CC1=CCC2(C1C3C(C(C=C2C)OC(=O)C)C(=C)C(=O)O3)OO
• InChI: InChI=1S/C17H20O6/c1-8-5-6-17(23-20)9(2)7-12(21-11(4)18)13-10(3)16(19)22-15(13)14(8)17/h5,7,12-15,20H,3,6H2,1-2,4H3
• InChI Key: BFENHNFSFSAWFO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9738	97.38%
Caco-2	+	0.5622	56.22%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5547	55.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9000	90.00%
OATP1B3 inhibitior	+	0.8757	87.57%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8338	83.38%
P-glycoprotein inhibitior	-	0.7727	77.27%
P-glycoprotein substrate	-	0.7487	74.87%
CYP3A4 substrate	+	0.6485	64.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.6792	67.92%
CYP2C9 inhibition	-	0.8336	83.36%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.6559	65.59%
CYP2C8 inhibition	-	0.6690	66.90%
CYP inhibitory promiscuity	-	0.9343	93.43%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.8625	86.25%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9579	95.79%
Eye irritation	-	0.8035	80.35%
Skin irritation	-	0.6245	62.45%
Skin corrosion	-	0.8472	84.72%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4333	43.33%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6878	68.78%
skin sensitisation	-	0.7087	70.87%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7111	71.11%
Acute Oral Toxicity (c)	II	0.4371	43.71%
Estrogen receptor binding	+	0.6022	60.22%
Androgen receptor binding	+	0.5413	54.13%
Thyroid receptor binding	+	0.5461	54.61%
Glucocorticoid receptor binding	-	0.5054	50.54%
Aromatase binding	-	0.6981	69.81%
PPAR gamma	+	0.5490	54.90%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9674	96.74%

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	96.68%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.49%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.43%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.19%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.03%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.24%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.14%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.38%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.20%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	80.68%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	80.11%	91.19%

Plants that contains it

• Artemisia gmelinii
• Schistostephium rotundifolium

Cross-Links

• PubChem: 162933220
• LOTUS: LTS0168070
• wikiData: Q104934063