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

Details

• Internal ID: b1e96bcd-3b9e-4e29-8c6d-f72dae8de81b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6a,9-dihydroperoxy-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)OO)OO)OC(=O)C2=C)OC(=O)C
• SMILES (Isomeric): CC1=CC(C2C(C3C1(C=CC3(C)OO)OO)OC(=O)C2=C)OC(=O)C
• InChI: InChI=1S/C17H20O8/c1-8-7-11(22-10(3)18)12-9(2)15(19)23-13(12)14-16(4,24-20)5-6-17(8,14)25-21/h5-7,11-14,20-21H,2H2,1,3-4H3
• InChI Key: ULMOSSRIWXLLCA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.30 g/mol
• Exact Mass: 352.11581759 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9405	94.05%
Caco-2	+	0.5080	50.80%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5650	56.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8318	83.18%
OATP1B3 inhibitior	+	0.9140	91.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6907	69.07%
P-glycoprotein inhibitior	-	0.6508	65.08%
P-glycoprotein substrate	-	0.7419	74.19%
CYP3A4 substrate	+	0.6496	64.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8950	89.50%
CYP3A4 inhibition	-	0.7867	78.67%
CYP2C9 inhibition	-	0.8302	83.02%
CYP2C19 inhibition	-	0.8208	82.08%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.7265	72.65%
CYP2C8 inhibition	-	0.6220	62.20%
CYP inhibitory promiscuity	-	0.8511	85.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7968	79.68%
Carcinogenicity (trinary)	Non-required	0.4280	42.80%
Eye corrosion	-	0.9320	93.20%
Eye irritation	-	0.7599	75.99%
Skin irritation	-	0.6653	66.53%
Skin corrosion	-	0.8787	87.87%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4847	48.47%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.7200	72.00%
skin sensitisation	-	0.7420	74.20%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7773	77.73%
Acute Oral Toxicity (c)	III	0.4220	42.20%
Estrogen receptor binding	+	0.6338	63.38%
Androgen receptor binding	+	0.5776	57.76%
Thyroid receptor binding	+	0.6195	61.95%
Glucocorticoid receptor binding	+	0.5542	55.42%
Aromatase binding	-	0.5986	59.86%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7118	71.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9716	97.16%

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	95.41%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	90.57%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.91%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.17%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.05%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.80%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.11%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.68%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.43%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.37%	91.19%

Plants that contains it

• Artemisia afra

Cross-Links

• PubChem: 14021330
• LOTUS: LTS0259921
• wikiData: Q105275228