[(3aR,4R,6aS,9aR,9bS)-6a-hydroperoxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-[[(E)-2-(hydroxymethyl)but-2-enoyl]oxymethyl]but-2-enoate

Details

• Internal ID: 5a28ff63-ee27-4fba-94c5-d165fb4d95c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aS,9aR,9bS)-6a-hydroperoxy-6,9-dimethyl-3-methylidene-2-oxo-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-[[(E)-2-(hydroxymethyl)but-2-enoyl]oxymethyl]but-2-enoate
• SMILES (Canonical): CC=C(CO)C(=O)OCC(=CCO)C(=O)OC1C=C(C2(CC=C(C2C3C1C(=C)C(=O)O3)C)OO)C
• SMILES (Isomeric): C/C=C(\CO)/C(=O)OC/C(=C\CO)/C(=O)O[C@@H]1C=C([C@@]2(CC=C([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C)OO)C
• InChI: InChI=1S/C25H30O10/c1-5-16(11-27)23(29)32-12-17(7-9-26)24(30)33-18-10-14(3)25(35-31)8-6-13(2)20(25)21-19(18)15(4)22(28)34-21/h5-7,10,18-21,26-27,31H,4,8-9,11-12H2,1-3H3/b16-5+,17-7+/t18-,19-,20-,21+,25-/m1/s1
• InChI Key: FWGSHFYJMWZSAS-ASPSGQCQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₀
• Molecular Weight: 490.50 g/mol
• Exact Mass: 490.18389715 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9186	91.86%
Caco-2	-	0.8176	81.76%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6601	66.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8713	87.13%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9454	94.54%
P-glycoprotein inhibitior	+	0.6557	65.57%
P-glycoprotein substrate	+	0.5113	51.13%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8828	88.28%
CYP3A4 inhibition	-	0.7246	72.46%
CYP2C9 inhibition	-	0.7766	77.66%
CYP2C19 inhibition	-	0.7745	77.45%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.7138	71.38%
CYP2C8 inhibition	+	0.5727	57.27%
CYP inhibitory promiscuity	-	0.8906	89.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.9399	93.99%
Skin irritation	-	0.6855	68.55%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7123	71.23%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5345	53.45%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4394	43.94%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	+	0.6556	65.56%
Thyroid receptor binding	-	0.4895	48.95%
Glucocorticoid receptor binding	+	0.7759	77.59%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.6199	61.99%
Honey bee toxicity	-	0.7576	75.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9840	98.40%

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	97.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.13%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.41%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.24%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.83%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.66%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.24%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.78%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.42%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	85.59%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.28%	94.00%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.44%	91.76%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.21%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.27%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.06%	91.07%

Plants that contains it

• Hymenopappus scabiosaeus

Cross-Links

• PubChem: 13970313
• LOTUS: LTS0023787
• wikiData: Q105003223