[(3aR,4R,6R,8R,8aR,9aR)-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] (2R)-2-methylbutanoate

Details

• Internal ID: fd921d01-319f-43a8-bf9e-b25f1e4ed72a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4R,6R,8R,8aR,9aR)-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] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(CC3C(C(C2=C1C)OC(=O)C(=C)C)C(=C)C(=O)O3)C)O
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1C[C@H]([C@@]2(C[C@@H]3[C@H]([C@H](C2=C1C)OC(=O)C(=C)C)C(=C)C(=O)O3)C)O
• InChI: InChI=1S/C24H32O7/c1-8-12(4)22(27)29-15-9-17(25)24(7)10-16-18(14(6)23(28)30-16)20(19(24)13(15)5)31-21(26)11(2)3/h12,15-18,20,25H,2,6,8-10H2,1,3-5,7H3/t12-,15-,16-,17-,18-,20-,24+/m1/s1
• InChI Key: UGYZWRRXLCDUFR-UOIUKYRCSA-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: 3.00
• 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	+	0.9971	99.71%
Caco-2	-	0.5563	55.63%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5803	58.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8643	86.43%
OATP1B3 inhibitior	+	0.9011	90.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6391	63.91%
P-glycoprotein inhibitior	+	0.6416	64.16%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6725	67.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	+	0.7473	74.73%
CYP2C9 inhibition	-	0.7732	77.32%
CYP2C19 inhibition	-	0.8271	82.71%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.8123	81.23%
CYP2C8 inhibition	+	0.5142	51.42%
CYP inhibitory promiscuity	-	0.7758	77.58%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5066	50.66%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8558	85.58%
Skin irritation	+	0.5365	53.65%
Skin corrosion	-	0.9136	91.36%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6327	63.27%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6178	61.78%
skin sensitisation	-	0.7528	75.28%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6488	64.88%
Acute Oral Toxicity (c)	III	0.5008	50.08%
Estrogen receptor binding	+	0.7340	73.40%
Androgen receptor binding	+	0.6487	64.87%
Thyroid receptor binding	+	0.5521	55.21%
Glucocorticoid receptor binding	+	0.7905	79.05%
Aromatase binding	+	0.5252	52.52%
PPAR gamma	+	0.6162	61.62%
Honey bee toxicity	-	0.5405	54.05%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9975	99.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.50%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.92%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.56%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.62%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.87%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	89.41%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	88.87%	90.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.91%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.69%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.47%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.51%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.44%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.17%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.85%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.80%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	82.60%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.53%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.16%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.50%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.55%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.39%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.30%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.20%	97.14%

Plants that contains it

• Wedelia hookeriana

Cross-Links

• PubChem: 163098824
• LOTUS: LTS0222840
• wikiData: Q105272659