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

Details

• Internal ID: 9cec6cde-6fb6-4a8d-94fa-db3dd75dbbe6
• 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-6-(2-methylpropanoyloxy)-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)C(C)C)C)C)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2C(CC3(C1=C(C(CC3O)OC(=O)C(C)C)C)C)OC(=O)C2=C
• InChI: InChI=1S/C24H32O7/c1-8-12(4)22(27)31-20-18-14(6)23(28)30-16(18)10-24(7)17(25)9-15(13(5)19(20)24)29-21(26)11(2)3/h8,11,15-18,20,25H,6,9-10H2,1-5,7H3
• InChI Key: MDYWSHZLWAQVIX-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: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	-	0.5378	53.78%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7248	72.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	-	0.2453	24.53%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5231	52.31%
P-glycoprotein inhibitior	+	0.6799	67.99%
P-glycoprotein substrate	-	0.5968	59.68%
CYP3A4 substrate	+	0.6729	67.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	+	0.5979	59.79%
CYP2C9 inhibition	-	0.7490	74.90%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	-	0.9594	95.94%
CYP1A2 inhibition	-	0.7829	78.29%
CYP2C8 inhibition	-	0.5627	56.27%
CYP inhibitory promiscuity	-	0.8871	88.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4997	49.97%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8830	88.30%
Skin irritation	-	0.5359	53.59%
Skin corrosion	-	0.9117	91.17%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4175	41.75%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6803	68.03%
skin sensitisation	-	0.6872	68.72%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7924	79.24%
Acute Oral Toxicity (c)	I	0.4154	41.54%
Estrogen receptor binding	+	0.7341	73.41%
Androgen receptor binding	+	0.6435	64.35%
Thyroid receptor binding	+	0.5208	52.08%
Glucocorticoid receptor binding	+	0.7424	74.24%
Aromatase binding	-	0.5111	51.11%
PPAR gamma	+	0.6121	61.21%
Honey bee toxicity	+	0.5928	59.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	95.91%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.62%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.14%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.88%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.72%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.38%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	89.23%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	88.16%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.99%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.50%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.08%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.85%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.26%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.24%	96.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.24%	95.71%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.18%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.83%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.21%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.20%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.02%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.31%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.18%	92.62%

Plants that contains it

• Aspilia foliosa

Cross-Links

• PubChem: 162976657
• LOTUS: LTS0270896
• wikiData: Q105162033