(3aR,4S,6aS,9R,9aS,9bS)-6a,9-dihydroperoxy-4-hydroxy-9-methyl-3,6-dimethylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 899c9f71-882b-48fc-a922-9d0360496d24
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aS,9R,9aS,9bS)-6a,9-dihydroperoxy-4-hydroxy-9-methyl-3,6-dimethylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• InChI: InChI=1S/C15H18O7/c1-7-6-9(16)10-8(2)13(17)20-11(10)12-14(3,21-18)4-5-15(7,12)22-19/h4-5,9-12,16,18-19H,1-2,6H2,3H3/t9-,10+,11-,12-,14+,15+/m0/s1
• InChI Key: BGIAGGJXJKYPSM-ABBQYLIMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₇
• Molecular Weight: 310.30 g/mol
• Exact Mass: 310.10525291 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9438	94.38%
Caco-2	-	0.6797	67.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5037	50.37%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8768	87.68%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9649	96.49%
P-glycoprotein inhibitior	-	0.8535	85.35%
P-glycoprotein substrate	-	0.7839	78.39%
CYP3A4 substrate	+	0.5862	58.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8365	83.65%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8238	82.38%
CYP2C19 inhibition	-	0.7534	75.34%
CYP2D6 inhibition	-	0.9105	91.05%
CYP1A2 inhibition	-	0.7595	75.95%
CYP2C8 inhibition	-	0.8642	86.42%
CYP inhibitory promiscuity	-	0.8105	81.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8364	83.64%
Carcinogenicity (trinary)	Non-required	0.4474	44.74%
Eye corrosion	-	0.9446	94.46%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.6780	67.80%
Skin corrosion	-	0.8316	83.16%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5857	58.57%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.7157	71.57%
skin sensitisation	-	0.7553	75.53%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8206	82.06%
Acute Oral Toxicity (c)	III	0.4447	44.47%
Estrogen receptor binding	-	0.5369	53.69%
Androgen receptor binding	+	0.5939	59.39%
Thyroid receptor binding	+	0.6450	64.50%
Glucocorticoid receptor binding	+	0.6982	69.82%
Aromatase binding	-	0.5082	50.82%
PPAR gamma	-	0.5379	53.79%
Honey bee toxicity	-	0.6768	67.68%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8656	86.56%

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	98.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.44%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.32%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.77%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.56%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.33%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.25%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.94%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.84%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.57%	83.82%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	80.64%	92.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.47%	92.94%

Plants that contains it

• Artemisia afra

Cross-Links

• PubChem: 163190846
• LOTUS: LTS0184333
• wikiData: Q105147102