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

Details

• Internal ID: da21453e-fd90-46a8-bed8-e3be8c94789c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [8-hydroxy-5,8a-dimethyl-3-methylidene-4-(2-methylprop-2-enoyloxy)-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-6-yl] 3-methylbutanoate
• SMILES (Canonical): CC1=C2C(C3C(CC2(C(CC1OC(=O)CC(C)C)O)C)OC(=O)C3=C)OC(=O)C(=C)C
• SMILES (Isomeric): CC1=C2C(C3C(CC2(C(CC1OC(=O)CC(C)C)O)C)OC(=O)C3=C)OC(=O)C(=C)C
• InChI: InChI=1S/C24H32O7/c1-11(2)8-18(26)29-15-9-17(25)24(7)10-16-19(14(6)23(28)30-16)21(20(24)13(15)5)31-22(27)12(3)4/h11,15-17,19,21,25H,3,6,8-10H2,1-2,4-5,7H3
• InChI Key: HKQLOIUOHKPLBC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.21480336 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.02
• 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	-	0.6119	61.19%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8735	87.35%
OATP1B3 inhibitior	-	0.3343	33.43%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5388	53.88%
P-glycoprotein inhibitior	+	0.6224	62.24%
P-glycoprotein substrate	+	0.5441	54.41%
CYP3A4 substrate	+	0.6794	67.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
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	+	0.4491	44.91%
CYP inhibitory promiscuity	-	0.8644	86.44%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5755	57.55%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.8349	83.49%
Skin irritation	-	0.5136	51.36%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5882	58.82%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6428	64.28%
skin sensitisation	-	0.7241	72.41%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7820	78.20%
Acute Oral Toxicity (c)	I	0.5605	56.05%
Estrogen receptor binding	+	0.6824	68.24%
Androgen receptor binding	+	0.6240	62.40%
Thyroid receptor binding	+	0.5286	52.86%
Glucocorticoid receptor binding	+	0.7889	78.89%
Aromatase binding	+	0.5498	54.98%
PPAR gamma	+	0.6171	61.71%
Honey bee toxicity	-	0.5149	51.49%
Biodegradation	-	0.7500	75.00%
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	95.38%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.93%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.38%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.19%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.08%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.05%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	86.85%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	86.24%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.94%	91.49%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.04%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	84.52%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	83.92%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.44%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.15%	96.38%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.80%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.15%	94.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.03%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.43%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.34%	97.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.02%	96.95%

Plants that contains it

• Wedelia hookeriana

Cross-Links

• PubChem: 162955304
• LOTUS: LTS0148797
• wikiData: Q105029863