(9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl) 3,4-dihydroxy-2-methylidenebutanoate

Details

• Internal ID: af6c55d3-71bf-4e96-8367-b67a6c15c747
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl) 3,4-dihydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC12CC(C3C(C1C(CCC2O)C=O)OC(=O)C3=C)OC(=O)C(=C)C(CO)O
• SMILES (Isomeric): CC12CC(C3C(C1C(CCC2O)C=O)OC(=O)C3=C)OC(=O)C(=C)C(CO)O
• InChI: InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3
• InChI Key: OZJAAHIGUMFSHY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.16276778 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.10
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.7077	70.77%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8121	81.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8778	87.78%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6095	60.95%
BSEP inhibitior	-	0.8768	87.68%
P-glycoprotein inhibitior	-	0.6911	69.11%
P-glycoprotein substrate	-	0.5231	52.31%
CYP3A4 substrate	+	0.6826	68.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.6309	63.09%
CYP2C9 inhibition	-	0.8234	82.34%
CYP2C19 inhibition	-	0.8770	87.70%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.8088	80.88%
CYP2C8 inhibition	-	0.5968	59.68%
CYP inhibitory promiscuity	-	0.9345	93.45%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9134	91.34%
Skin irritation	+	0.5183	51.83%
Skin corrosion	-	0.9287	92.87%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4158	41.58%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5464	54.64%
skin sensitisation	-	0.8955	89.55%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5925	59.25%
Acute Oral Toxicity (c)	III	0.5009	50.09%
Estrogen receptor binding	+	0.8655	86.55%
Androgen receptor binding	+	0.6455	64.55%
Thyroid receptor binding	+	0.5940	59.40%
Glucocorticoid receptor binding	+	0.7440	74.40%
Aromatase binding	+	0.7214	72.14%
PPAR gamma	+	0.6399	63.99%
Honey bee toxicity	-	0.7041	70.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9909	99.09%

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	98.40%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.74%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.22%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.76%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	89.25%	83.82%
CHEMBL1871	P10275	Androgen Receptor	88.13%	96.43%
CHEMBL204	P00734	Thrombin	87.29%	96.01%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.26%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.56%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.40%	96.47%
CHEMBL221	P23219	Cyclooxygenase-1	86.02%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.86%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.47%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.25%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.53%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.05%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	81.31%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.86%	95.89%
CHEMBL5028	O14672	ADAM10	80.30%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.27%	100.00%

Plants that contains it

• Centaurea attica
• Centaurea spinosa

Cross-Links

• PubChem: 73069811
• LOTUS: LTS0066877
• wikiData: Q105203859