(6a-Hydroperoxy-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,9a,9b-tetrahydroazuleno[4,5-b]furan-4-yl) acetate

Details

• Internal ID: 12bf81f5-ae1b-415a-b629-668511454f19
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6a-hydroperoxy-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,9a,9b-tetrahydroazuleno[4,5-b]furan-4-yl) acetate
• SMILES (Canonical): CC1=CC(C2C(C3C1(C=CC3(C)O)OO)OC(=O)C2=C)OC(=O)C
• SMILES (Isomeric): CC1=CC(C2C(C3C1(C=CC3(C)O)OO)OC(=O)C2=C)OC(=O)C
• InChI: InChI=1S/C17H20O7/c1-8-7-11(22-10(3)18)12-9(2)15(19)23-13(12)14-16(4,20)5-6-17(8,14)24-21/h5-7,11-14,20-21H,2H2,1,3-4H3
• InChI Key: UPPMAHKCRBJIQR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₇
• Molecular Weight: 336.30 g/mol
• Exact Mass: 336.12090297 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9463	94.63%
Caco-2	-	0.5945	59.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5437	54.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8387	83.87%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8182	81.82%
P-glycoprotein inhibitior	-	0.6824	68.24%
P-glycoprotein substrate	-	0.7932	79.32%
CYP3A4 substrate	+	0.6474	64.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8988	89.88%
CYP3A4 inhibition	-	0.7880	78.80%
CYP2C9 inhibition	-	0.8443	84.43%
CYP2C19 inhibition	-	0.8325	83.25%
CYP2D6 inhibition	-	0.9358	93.58%
CYP1A2 inhibition	-	0.7360	73.60%
CYP2C8 inhibition	-	0.5999	59.99%
CYP inhibitory promiscuity	-	0.8341	83.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8568	85.68%
Carcinogenicity (trinary)	Non-required	0.4280	42.80%
Eye corrosion	-	0.9356	93.56%
Eye irritation	-	0.8024	80.24%
Skin irritation	-	0.6450	64.50%
Skin corrosion	-	0.8791	87.91%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5160	51.60%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.7075	70.75%
skin sensitisation	-	0.7159	71.59%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7867	78.67%
Acute Oral Toxicity (c)	III	0.4058	40.58%
Estrogen receptor binding	+	0.5585	55.85%
Androgen receptor binding	+	0.5402	54.02%
Thyroid receptor binding	+	0.5534	55.34%
Glucocorticoid receptor binding	-	0.6280	62.80%
Aromatase binding	-	0.6667	66.67%
PPAR gamma	-	0.5194	51.94%
Honey bee toxicity	-	0.7192	71.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9684	96.84%

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	96.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.60%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.26%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.46%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.09%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.81%	97.28%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.04%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.87%	93.65%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.29%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.89%	94.00%

Plants that contains it

• Artemisia afra

Cross-Links

• PubChem: 14021333
• LOTUS: LTS0051878
• wikiData: Q105276929