[8-hydroxy-5,8a-dimethyl-6-(3-methylbutanoyloxy)-3-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-4-yl] 2-methylbut-2-enoate

Details

• Internal ID: 81198235-a3be-4f1c-8fb5-87562bfe72bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [8-hydroxy-5,8a-dimethyl-6-(3-methylbutanoyloxy)-3-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-4-yl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(CC3(C1=C(C(CC3O)OC(=O)CC(C)C)C)C)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2C(CC3(C1=C(C(CC3O)OC(=O)CC(C)C)C)C)OC(=O)C2=C
• InChI: InChI=1S/C25H34O7/c1-8-13(4)23(28)32-22-20-15(6)24(29)31-17(20)11-25(7)18(26)10-16(14(5)21(22)25)30-19(27)9-12(2)3/h8,12,16-18,20,22,26H,6,9-11H2,1-5,7H3
• InChI Key: XGECHFRUBTTWOQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₇
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.23045342 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	-	0.5978	59.78%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8495	84.95%
OATP1B3 inhibitior	-	0.3343	33.43%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6227	62.27%
P-glycoprotein inhibitior	+	0.7398	73.98%
P-glycoprotein substrate	+	0.5233	52.33%
CYP3A4 substrate	+	0.6755	67.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	+	0.6256	62.56%
CYP2C9 inhibition	-	0.7109	71.09%
CYP2C19 inhibition	-	0.8241	82.41%
CYP2D6 inhibition	-	0.9639	96.39%
CYP1A2 inhibition	-	0.8340	83.40%
CYP2C8 inhibition	-	0.5575	55.75%
CYP inhibitory promiscuity	-	0.8644	86.44%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5755	57.55%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.8898	88.98%
Skin irritation	-	0.5136	51.36%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4470	44.70%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6428	64.28%
skin sensitisation	-	0.7241	72.41%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7407	74.07%
Acute Oral Toxicity (c)	I	0.5605	56.05%
Estrogen receptor binding	+	0.7131	71.31%
Androgen receptor binding	+	0.6176	61.76%
Thyroid receptor binding	+	0.5219	52.19%
Glucocorticoid receptor binding	+	0.7816	78.16%
Aromatase binding	+	0.5480	54.80%
PPAR gamma	+	0.6650	66.50%
Honey bee toxicity	-	0.4806	48.06%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.09%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.40%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.53%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.76%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.75%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.40%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.70%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.09%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.78%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.05%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.70%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	84.65%	94.73%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.62%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	84.31%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.77%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.49%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.37%	94.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.26%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.59%	99.23%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	80.50%	92.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.39%	91.07%

Plants that contains it

• Aspilia foliosa

Cross-Links

• PubChem: 163038808
• LOTUS: LTS0103325
• wikiData: Q105327546