9-Hydroperoxy-6a-hydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 888a6ec9-64b2-4942-98fe-c0ca15fe8863
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 9-hydroperoxy-6a-hydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=C)C3(C=CC(C3C2OC1=O)(C)OO)O
• SMILES (Isomeric): CC1C2CCC(=C)C3(C=CC(C3C2OC1=O)(C)OO)O
• InChI: InChI=1S/C15H20O5/c1-8-4-5-10-9(2)13(16)19-11(10)12-14(3,20-18)6-7-15(8,12)17/h6-7,9-12,17-18H,1,4-5H2,2-3H3
• InChI Key: RIWSVTDIMBKNHT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9468	94.68%
Caco-2	-	0.6266	62.66%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5646	56.46%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9003	90.03%
OATP1B3 inhibitior	+	0.9030	90.30%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9104	91.04%
P-glycoprotein inhibitior	-	0.9046	90.46%
P-glycoprotein substrate	-	0.8035	80.35%
CYP3A4 substrate	+	0.6266	62.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.7647	76.47%
CYP2C9 inhibition	-	0.7172	71.72%
CYP2C19 inhibition	-	0.6800	68.00%
CYP2D6 inhibition	-	0.8942	89.42%
CYP1A2 inhibition	+	0.5485	54.85%
CYP2C8 inhibition	-	0.8565	85.65%
CYP inhibitory promiscuity	-	0.7458	74.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8925	89.25%
Carcinogenicity (trinary)	Non-required	0.5311	53.11%
Eye corrosion	-	0.9645	96.45%
Eye irritation	-	0.9426	94.26%
Skin irritation	-	0.6216	62.16%
Skin corrosion	-	0.8304	83.04%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4166	41.66%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6982	69.82%
skin sensitisation	-	0.7356	73.56%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5093	50.93%
Acute Oral Toxicity (c)	III	0.3996	39.96%
Estrogen receptor binding	+	0.5508	55.08%
Androgen receptor binding	+	0.6024	60.24%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.7138	71.38%
Aromatase binding	-	0.5807	58.07%
PPAR gamma	-	0.6243	62.43%
Honey bee toxicity	-	0.7908	79.08%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9681	96.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.29%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.25%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.30%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.43%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.30%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.14%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.48%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.42%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.64%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.50%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.29%	92.94%
CHEMBL2581	P07339	Cathepsin D	80.28%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.11%	89.00%

Plants that contains it

• Artemisia adamsii

Cross-Links

• PubChem: 162951658
• LOTUS: LTS0067257
• wikiData: Q105237224